# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl #TrackingRef 'c2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H27 N O4' _chemical_formula_weight 405.48 _chemical_absolute_configuration unk loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 27.119(4) _cell_length_b 10.6814(16) _cell_length_c 21.580(4) _cell_angle_alpha 90.00 _cell_angle_beta 131.850(3) _cell_angle_gamma 90.00 _cell_volume 4656.5(13) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3745 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 22.1 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.157 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1728 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.938 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_process_details 'SADABS (Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker axs kappa apex2 CCD Diffractometer' _diffrn_measurement_method '\w and \f scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10598 _diffrn_reflns_av_R_equivalents 0.0350 _diffrn_reflns_av_sigmaI/netI 0.0593 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 22.60 _reflns_number_total 5560 _reflns_number_gt 3736 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'APEX2/SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2004)' _computing_structure_solution 'SIR92 (Altornare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0522P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00059(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 2.0(15) _refine_ls_number_reflns 5560 _refine_ls_number_parameters 546 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0780 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1177 _refine_ls_wR_factor_gt 0.1042 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.052 0.000 195 28 ' ' 2 0.500 0.009 1.000 195 28 ' ' 3 0.500 0.092 0.500 23 3 ' ' 4 0.000 0.592 0.500 23 3 ' ' _platon_squeeze_details ; ; loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6980(2) 0.9789(4) 0.9546(3) 0.0716(12) Uani 1 1 d . . . H1 H 0.7179 0.9155 0.9983 0.086 Uiso 1 1 calc R . . C1A C 0.6941(2) -0.0107(5) 0.3227(3) 0.0782(13) Uani 1 1 d . . . H1A1 H 0.6652 -0.0718 0.3180 0.094 Uiso 1 1 calc R . . H1A2 H 0.7080 -0.0442 0.2947 0.094 Uiso 1 1 calc R . . C2 C 0.5891(2) 0.8874(5) 0.8781(3) 0.0886(14) Uani 1 1 d . . . H2A H 0.6096 0.8332 0.9258 0.106 Uiso 1 1 calc R . . H2B H 0.5539 0.8408 0.8285 0.106 Uiso 1 1 calc R . . C2A C 0.6566(2) 0.1079(5) 0.2812(3) 0.0815(13) Uani 1 1 d . . . H7V H 0.6868 0.1675 0.2866 0.098 Uiso 1 1 calc R . . C3 C 0.5610(3) 0.9992(7) 0.8858(4) 0.1115(18) Uani 1 1 d . . . H3 H 0.5393 1.0505 0.8359 0.134 Uiso 1 1 calc R . . C3A C 0.6349(2) 0.1646(4) 0.3243(3) 0.0811(13) Uani 1 1 d . . . H3A H 0.6212 0.2516 0.3064 0.097 Uiso 1 1 calc R . . C4 C 0.6136(3) 1.0776(5) 0.9595(4) 0.1081(18) Uani 1 1 d . . . H4 H 0.5952 1.1599 0.9544 0.130 Uiso 1 1 calc R . . C4A C 0.5824(2) 0.1265(5) 0.3715(3) 0.0871(14) Uani 1 1 d . . . C5 C 0.7016(4) 1.0799(5) 1.1029(4) 0.1150(19) Uani 1 1 d . . . C5A C 0.5377(2) 0.2371(6) 0.3465(3) 0.128(2) Uani 1 1 d . . . H5A1 H 0.5501 0.3056 0.3305 0.193 Uiso 1 1 calc R . . H5A2 H 0.5419 0.2620 0.3926 0.193 Uiso 1 1 calc R . . H5A3 H 0.4926 0.2141 0.3004 0.193 Uiso 1 1 calc R . . C6 C 0.6933(4) 1.1980(6) 1.1342(5) 0.174(3) Uani 1 1 d . . . H6A H 0.6694 1.2594 1.0905 0.262 Uiso 1 1 calc R . . H6B H 0.7361 1.2306 1.1808 0.262 Uiso 1 1 calc R . . H6C H 0.6691 1.1788 1.1510 0.262 Uiso 1 1 calc R . . C6A C 0.5616(3) 0.0117(6) 0.3916(3) 0.122(2) Uani 1 1 d . . . H6A1 H 0.5181 -0.0141 0.3426 0.183 Uiso 1 1 calc R . . H6A2 H 0.5613 0.0323 0.4347 0.183 Uiso 1 1 calc R . . H6A3 H 0.5924 -0.0552 0.4101 0.183 Uiso 1 1 calc R . . C7 C 0.7469(4) 0.9851(8) 1.1685(3) 0.165(3) Uani 1 1 d . . . H7A H 0.7255 0.9456 1.1851 0.248 Uiso 1 1 calc R . . H7B H 0.7867 1.0255 1.2157 0.248 Uiso 1 1 calc R . . H7C H 0.7577 0.9231 1.1470 0.248 Uiso 1 1 calc R . . C7A C 0.68738(18) 0.1587(4) 0.4188(2) 0.0638(10) Uani 1 1 d . . . H8V H 0.7156 0.2333 0.4406 0.077 Uiso 1 1 calc R . . C8 C 0.6774(3) 1.0947(4) 0.9771(3) 0.0931(15) Uani 1 1 d . . . H8 H 0.6736 1.1684 0.9472 0.112 Uiso 1 1 calc R . . C8A C 0.72998(18) 0.0413(3) 0.4558(2) 0.0570(10) Uani 1 1 d . . . H8A H 0.7038 -0.0283 0.4503 0.068 Uiso 1 1 calc R . . C9 C 0.6601(2) 0.8114(4) 0.8549(3) 0.0794(12) Uani 1 1 d . . . H9A H 0.7018 0.8296 0.8694 0.095 Uiso 1 1 calc R . . H9B H 0.6672 0.7417 0.8889 0.095 Uiso 1 1 calc R . . C9A C 0.7925(2) -0.1069(4) 0.4459(3) 0.0741(12) Uani 1 1 d . . . H9A1 H 0.7637 -0.1765 0.4321 0.089 Uiso 1 1 calc R . . H9A2 H 0.8253 -0.0998 0.5060 0.089 Uiso 1 1 calc R . . C10 C 0.6095(2) 0.7753(4) 0.7649(3) 0.0740(12) Uani 1 1 d . . . C10A C 0.8272(2) -0.1358(4) 0.4149(2) 0.0690(11) Uani 1 1 d . . . C11 C 0.6050(3) 0.8429(5) 0.7070(3) 0.0902(14) Uani 1 1 d . . . H11 H 0.6338 0.9091 0.7237 0.108 Uiso 1 1 calc R . . C11A C 0.8697(3) -0.0526(6) 0.4233(3) 0.1170(19) Uani 1 1 d . . . H11A H 0.8770 0.0248 0.4479 0.140 Uiso 1 1 calc R . . C12 C 0.5572(3) 0.8117(6) 0.6238(4) 0.1089(17) Uani 1 1 d . . . H12 H 0.5541 0.8573 0.5846 0.131 Uiso 1 1 calc R . . C12A C 0.9022(3) -0.0810(8) 0.3958(4) 0.143(3) Uani 1 1 d . . . H12A H 0.9282 -0.0209 0.3981 0.171 Uiso 1 1 calc R . . C13 C 0.5135(3) 0.7123(7) 0.5977(4) 0.1040(17) Uani 1 1 d . . . H13 H 0.4810 0.6926 0.5415 0.125 Uiso 1 1 calc R . . C13A C 0.8960(3) -0.1948(8) 0.3659(4) 0.125(2) Uani 1 1 d . . . H13A H 0.9194 -0.2150 0.3497 0.150 Uiso 1 1 calc R . . C14 C 0.5191(3) 0.6463(5) 0.6545(4) 0.1017(16) Uani 1 1 d . . . H14 H 0.4906 0.5794 0.6377 0.122 Uiso 1 1 calc R . . C14A C 0.8561(3) -0.2810(6) 0.3589(4) 0.1191(19) Uani 1 1 d . . . H14A H 0.8523 -0.3605 0.3385 0.143 Uiso 1 1 calc R . . C15 C 0.5670(3) 0.6760(5) 0.7387(3) 0.0900(13) Uani 1 1 d . . . H15 H 0.5704 0.6286 0.7775 0.108 Uiso 1 1 calc R . . C15A C 0.8206(3) -0.2502(5) 0.3824(3) 0.0940(15) Uani 1 1 d . . . H15A H 0.7920 -0.3087 0.3757 0.113 Uiso 1 1 calc R . . C16 C 0.7482(2) 1.0208(4) 0.9505(3) 0.0668(11) Uani 1 1 d . . . C16A C 0.7876(2) 0.0669(3) 0.5475(2) 0.0594(10) Uani 1 1 d . . . C17 C 0.8182(3) 0.9928(4) 1.0159(3) 0.0824(13) Uani 1 1 d . . . C17A C 0.7902(2) 0.0267(4) 0.6125(3) 0.0637(11) Uani 1 1 d . . . C18 C 0.8434(3) 0.9197(5) 1.0865(3) 0.1007(16) Uani 1 1 d . . . H18 H 0.8141 0.8895 1.0916 0.121 Uiso 1 1 calc R . . C18A C 0.7413(3) -0.0522(4) 0.5971(3) 0.0832(13) Uani 1 1 d . . . H18A H 0.7076 -0.0814 0.5433 0.100 Uiso 1 1 calc R . . C19 C 0.9080(4) 0.8925(7) 1.1462(5) 0.141(3) Uani 1 1 d . . . H19 H 0.9224 0.8422 1.1908 0.169 Uiso 1 1 calc R . . C19A C 0.7418(3) -0.0877(4) 0.6593(4) 0.1074(18) Uani 1 1 d . . . H19A H 0.7095 -0.1406 0.6481 0.129 Uiso 1 1 calc R . . C20 C 0.9533(5) 0.9387(8) 1.1420(6) 0.172(4) Uani 1 1 d . . . H20 H 0.9980 0.9208 1.1847 0.206 Uiso 1 1 calc R . . C20A C 0.7925(5) -0.0413(6) 0.7392(4) 0.127(2) Uani 1 1 d . . . H20A H 0.7928 -0.0615 0.7813 0.153 Uiso 1 1 calc R . . C21 C 0.9342(4) 1.0087(8) 1.0776(7) 0.147(3) Uani 1 1 d . . . H21 H 0.9651 1.0376 1.0750 0.177 Uiso 1 1 calc R . . C21A C 0.8416(3) 0.0325(6) 0.7574(3) 0.1078(18) Uani 1 1 d . . . H21A H 0.8757 0.0590 0.8118 0.129 Uiso 1 1 calc R . . C22 C 0.8645(3) 1.0388(5) 1.0121(4) 0.1021(17) Uani 1 1 d . . . C22A C 0.8408(3) 0.0688(5) 0.6946(3) 0.0845(14) Uani 1 1 d . . . C23 C 0.8413(4) 1.1129(7) 0.9430(6) 0.123(2) Uani 1 1 d . . . H23 H 0.8718 1.1459 0.9407 0.148 Uiso 1 1 calc R . . C23A C 0.8904(3) 0.1489(5) 0.7114(3) 0.0963(16) Uani 1 1 d . . . H23A H 0.9239 0.1781 0.7653 0.116 Uiso 1 1 calc R . . C24 C 0.7759(4) 1.1373(5) 0.8799(4) 0.1105(19) Uani 1 1 d . . . H24 H 0.7619 1.1833 0.8340 0.133 Uiso 1 1 calc R . . C24A C 0.8899(2) 0.1834(4) 0.6513(3) 0.0848(13) Uani 1 1 d . . . H24A H 0.9235 0.2341 0.6638 0.102 Uiso 1 1 calc R . . C25 C 0.7290(3) 1.0921(4) 0.8844(3) 0.0850(13) Uani 1 1 d . . . C25A C 0.8389(2) 0.1429(4) 0.5698(3) 0.0643(10) Uani 1 1 d . . . N1 N 0.63847(17) 0.9239(3) 0.8732(2) 0.0713(9) Uani 1 1 d . . . N1A N 0.75251(15) 0.0095(3) 0.41100(18) 0.0604(8) Uani 1 1 d . . . O1 O 0.51179(18) 0.9630(5) 0.8883(2) 0.1546(18) Uani 1 1 d . . . H1B H 0.4759 0.9570 0.8407 0.232 Uiso 1 1 calc R . . O1A O 0.60304(15) 0.0890(4) 0.19582(17) 0.1142(12) Uani 1 1 d . . . H1A H 0.6088 0.1296 0.1689 0.171 Uiso 1 1 calc R . . O2 O 0.6400(2) 1.0205(3) 1.0374(2) 0.1060(11) Uani 1 1 d . . . O2A O 0.58119(13) 0.0945(3) 0.30644(17) 0.0930(9) Uani 1 1 d . . . O3 O 0.72784(19) 1.1154(3) 1.0644(2) 0.1077(11) Uani 1 1 d . . . O3A O 0.64784(13) 0.1609(3) 0.44151(16) 0.0727(7) Uani 1 1 d . . . O4 O 0.6642(2) 1.1176(3) 0.8196(2) 0.1039(11) Uani 1 1 d . . . H4O H 0.6411 1.0653 0.8178 0.156 Uiso 1 1 calc R . . O4A O 0.84116(13) 0.1851(3) 0.51203(18) 0.0788(8) Uani 1 1 d . . . H4A H 0.8175 0.1411 0.4703 0.118 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.091(3) 0.067(3) 0.064(3) 0.017(2) 0.055(3) 0.012(2) C1A 0.086(3) 0.106(4) 0.070(3) -0.020(3) 0.064(3) -0.030(3) C2 0.081(3) 0.107(4) 0.076(3) 0.025(3) 0.051(3) 0.018(3) C2A 0.075(3) 0.114(4) 0.056(3) 0.007(3) 0.044(3) -0.013(3) C3 0.102(4) 0.152(6) 0.090(4) 0.040(4) 0.068(4) 0.033(4) C3A 0.066(3) 0.096(3) 0.073(3) 0.017(2) 0.043(3) -0.004(3) C4 0.164(5) 0.098(4) 0.139(5) 0.047(4) 0.133(5) 0.043(4) C4A 0.067(3) 0.119(4) 0.079(3) -0.001(3) 0.051(3) -0.011(3) C5 0.187(6) 0.090(4) 0.127(5) -0.038(4) 0.130(5) -0.047(4) C5A 0.092(4) 0.164(6) 0.100(4) 0.018(4) 0.052(4) 0.037(4) C6 0.301(9) 0.147(6) 0.238(8) -0.080(5) 0.247(8) -0.078(6) C6A 0.109(4) 0.155(5) 0.122(4) -0.016(4) 0.085(4) -0.043(4) C7 0.203(7) 0.182(7) 0.076(4) -0.004(5) 0.079(5) -0.055(6) C7A 0.059(3) 0.072(3) 0.060(3) 0.009(2) 0.040(2) 0.002(2) C8 0.163(5) 0.056(3) 0.131(5) 0.025(3) 0.127(4) 0.023(3) C8A 0.067(3) 0.060(3) 0.060(3) -0.0024(19) 0.048(2) -0.008(2) C9 0.074(3) 0.072(3) 0.065(3) 0.008(2) 0.035(3) 0.015(2) C9A 0.103(3) 0.069(3) 0.084(3) -0.010(2) 0.077(3) -0.013(3) C10 0.070(3) 0.073(3) 0.066(3) 0.008(2) 0.041(3) 0.011(2) C10A 0.084(3) 0.074(3) 0.072(3) -0.010(2) 0.061(3) -0.012(2) C11 0.104(4) 0.092(4) 0.076(4) 0.000(3) 0.061(3) -0.004(3) C11A 0.132(4) 0.120(4) 0.147(5) -0.058(4) 0.114(4) -0.053(4) C12 0.124(5) 0.123(5) 0.079(4) 0.014(3) 0.067(4) 0.020(4) C12A 0.152(6) 0.158(6) 0.203(7) -0.065(5) 0.154(6) -0.066(5) C13 0.088(4) 0.135(5) 0.089(4) -0.020(4) 0.058(3) -0.006(4) C13A 0.109(5) 0.180(7) 0.141(5) -0.028(5) 0.106(5) -0.013(4) C14 0.090(4) 0.117(4) 0.116(5) -0.028(4) 0.076(4) -0.018(3) C14A 0.164(6) 0.105(4) 0.149(5) -0.031(4) 0.130(5) -0.003(4) C15 0.091(4) 0.089(4) 0.092(4) -0.004(3) 0.062(3) -0.001(3) C15A 0.140(4) 0.078(3) 0.120(4) -0.025(3) 0.110(4) -0.015(3) C16 0.090(3) 0.060(3) 0.066(3) -0.007(2) 0.059(3) 0.002(2) C16A 0.069(3) 0.052(3) 0.066(3) 0.004(2) 0.048(3) 0.007(2) C17 0.105(4) 0.055(3) 0.096(4) -0.025(3) 0.070(4) -0.012(3) C17A 0.081(3) 0.062(3) 0.060(3) 0.011(2) 0.052(3) 0.020(2) C18 0.085(4) 0.067(3) 0.084(4) -0.012(3) 0.029(3) -0.007(3) C18A 0.134(4) 0.069(3) 0.084(3) 0.013(2) 0.088(3) 0.021(3) C19 0.077(5) 0.113(5) 0.144(6) -0.023(4) 0.037(5) -0.013(4) C19A 0.196(6) 0.064(3) 0.124(5) 0.013(3) 0.132(5) 0.017(3) C20 0.112(7) 0.124(7) 0.142(7) -0.025(5) 0.027(6) 0.005(5) C20A 0.243(8) 0.088(4) 0.112(5) 0.040(4) 0.144(6) 0.053(5) C21 0.090(6) 0.128(6) 0.191(8) -0.078(6) 0.079(6) -0.026(4) C21A 0.152(6) 0.100(5) 0.080(4) 0.015(3) 0.081(4) 0.036(4) C22 0.131(6) 0.084(4) 0.123(5) -0.039(3) 0.097(5) -0.030(4) C22A 0.119(4) 0.077(3) 0.065(4) 0.021(3) 0.065(4) 0.040(3) C23 0.142(6) 0.127(5) 0.175(7) -0.071(5) 0.136(6) -0.052(5) C23A 0.101(4) 0.096(4) 0.066(4) 0.000(3) 0.045(3) 0.028(3) C24 0.183(6) 0.091(4) 0.135(5) -0.010(4) 0.139(6) -0.016(4) C24A 0.056(3) 0.086(3) 0.077(4) -0.016(3) 0.030(3) 0.002(2) C25 0.125(4) 0.073(3) 0.089(4) -0.001(3) 0.085(4) 0.004(3) C25A 0.067(3) 0.058(3) 0.060(3) 0.004(2) 0.039(3) 0.014(2) N1 0.074(2) 0.076(2) 0.057(2) 0.0136(17) 0.041(2) 0.0156(19) N1A 0.070(2) 0.066(2) 0.056(2) -0.0016(17) 0.046(2) -0.0046(18) O1 0.109(3) 0.251(5) 0.144(3) 0.054(3) 0.101(3) 0.041(3) O1A 0.088(2) 0.200(4) 0.049(2) 0.007(2) 0.0430(19) -0.022(2) O2 0.155(3) 0.104(2) 0.104(3) 0.009(2) 0.105(3) -0.006(2) O2A 0.0667(19) 0.146(3) 0.071(2) -0.0085(19) 0.0475(18) -0.0233(19) O3 0.173(3) 0.094(2) 0.117(3) -0.027(2) 0.122(3) -0.030(2) O3A 0.0639(18) 0.088(2) 0.0701(19) 0.0006(15) 0.0463(18) -0.0028(15) O4 0.145(3) 0.090(2) 0.096(3) 0.0328(19) 0.089(3) 0.028(2) O4A 0.0727(19) 0.081(2) 0.084(2) -0.0055(15) 0.0524(18) -0.0119(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C16 1.491(6) . ? C1 N1 1.500(5) . ? C1 C8 1.563(6) . ? C1 H1 0.9800 . ? C1A N1A 1.470(5) . ? C1A C2A 1.491(6) . ? C1A H1A1 0.9700 . ? C1A H1A2 0.9700 . ? C2 N1 1.463(5) . ? C2 C3 1.485(7) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C2A O1A 1.405(4) . ? C2A C3A 1.521(6) . ? C2A H7V 0.9800 . ? C3 O1 1.424(6) . ? C3 C4 1.497(7) . ? C3 H3 0.9800 . ? C3A O2A 1.443(5) . ? C3A C7A 1.522(5) . ? C3A H3A 0.9800 . ? C4 O2 1.450(6) . ? C4 C8 1.515(7) . ? C4 H4 0.9800 . ? C4A O3A 1.410(5) . ? C4A O2A 1.425(5) . ? C4A C5A 1.512(7) . ? C4A C6A 1.527(7) . ? C5 O2 1.428(6) . ? C5 O3 1.458(6) . ? C5 C7 1.490(9) . ? C5 C6 1.517(8) . ? C5A H5A1 0.9600 . ? C5A H5A2 0.9600 . ? C5A H5A3 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C6A H6A1 0.9600 . ? C6A H6A2 0.9600 . ? C6A H6A3 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C7A O3A 1.446(4) . ? C7A C8A 1.521(5) . ? C7A H8V 0.9800 . ? C8 O3 1.425(6) . ? C8 H8 0.9800 . ? C8A N1A 1.487(4) . ? C8A C16A 1.519(5) . ? C8A H8A 0.9800 . ? C9 C10 1.500(6) . ? C9 N1 1.502(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9A N1A 1.483(5) . ? C9A C10A 1.506(5) . ? C9A H9A1 0.9700 . ? C9A H9A2 0.9700 . ? C10 C11 1.376(6) . ? C10 C15 1.379(6) . ? C10A C15A 1.360(6) . ? C10A C11A 1.370(6) . ? C11 C12 1.382(6) . ? C11 H11 0.9300 . ? C11A C12A 1.384(7) . ? C11A H11A 0.9300 . ? C12 C13 1.400(7) . ? C12 H12 0.9300 . ? C12A C13A 1.333(8) . ? C12A H12A 0.9300 . ? C13 C14 1.332(7) . ? C13 H13 0.9300 . ? C13A C14A 1.351(7) . ? C13A H13A 0.9300 . ? C14 C15 1.393(6) . ? C14 H14 0.9300 . ? C14A C15A 1.392(6) . ? C14A H14A 0.9300 . ? C15 H15 0.9300 . ? C15A H15A 0.9300 . ? C16 C25 1.375(6) . ? C16 C17 1.453(6) . ? C16A C25A 1.391(5) . ? C16A C17A 1.423(5) . ? C17 C22 1.400(7) . ? C17 C18 1.417(6) . ? C17A C22A 1.406(6) . ? C17A C18A 1.412(6) . ? C18 C19 1.342(7) . ? C18 H18 0.9300 . ? C18A C19A 1.386(6) . ? C18A H18A 0.9300 . ? C19 C20 1.384(12) . ? C19 H19 0.9300 . ? C19A C20A 1.396(8) . ? C19A H19A 0.9300 . ? C20 C21 1.339(11) . ? C20 H20 0.9300 . ? C20A C21A 1.359(8) . ? C20A H20A 0.9300 . ? C21 C22 1.452(9) . ? C21 H21 0.9300 . ? C21A C22A 1.397(7) . ? C21A H21A 0.9300 . ? C22 C23 1.411(9) . ? C22A C23A 1.422(7) . ? C23 C24 1.359(8) . ? C23 H23 0.9300 . ? C23A C24A 1.340(6) . ? C23A H23A 0.9300 . ? C24 C25 1.425(7) . ? C24 H24 0.9300 . ? C24A C25A 1.395(5) . ? C24A H24A 0.9300 . ? C25 O4 1.356(5) . ? C25A O4A 1.364(5) . ? O1 H1B 0.8200 . ? O1A H1A 0.8200 . ? O4 H4O 0.8200 . ? O4A H4A 0.8200 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 C1 N1 111.1(3) . . ? C16 C1 C8 108.1(3) . . ? N1 C1 C8 110.2(4) . . ? C16 C1 H1 109.1 . . ? N1 C1 H1 109.1 . . ? C8 C1 H1 109.1 . . ? N1A C1A C2A 111.5(4) . . ? N1A C1A H1A1 109.3 . . ? C2A C1A H1A1 109.3 . . ? N1A C1A H1A2 109.3 . . ? C2A C1A H1A2 109.3 . . ? H1A1 C1A H1A2 108.0 . . ? N1 C2 C3 110.9(4) . . ? N1 C2 H2A 109.5 . . ? C3 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? O1A C2A C1A 111.1(4) . . ? O1A C2A C3A 112.0(4) . . ? C1A C2A C3A 110.9(3) . . ? O1A C2A H7V 107.5 . . ? C1A C2A H7V 107.5 . . ? C3A C2A H7V 107.5 . . ? O1 C3 C2 110.5(5) . . ? O1 C3 C4 111.3(5) . . ? C2 C3 C4 111.8(4) . . ? O1 C3 H3 107.7 . . ? C2 C3 H3 107.7 . . ? C4 C3 H3 107.7 . . ? O2A C3A C2A 111.4(4) . . ? O2A C3A C7A 102.2(3) . . ? C2A C3A C7A 114.0(3) . . ? O2A C3A H3A 109.7 . . ? C2A C3A H3A 109.7 . . ? C7A C3A H3A 109.7 . . ? O2 C4 C3 112.4(5) . . ? O2 C4 C8 99.3(4) . . ? C3 C4 C8 117.0(4) . . ? O2 C4 H4 109.2 . . ? C3 C4 H4 109.2 . . ? C8 C4 H4 109.2 . . ? O3A C4A O2A 107.6(3) . . ? O3A C4A C5A 108.4(4) . . ? O2A C4A C5A 110.4(4) . . ? O3A C4A C6A 110.1(4) . . ? O2A C4A C6A 108.5(4) . . ? C5A C4A C6A 111.7(4) . . ? O2 C5 O3 104.2(4) . . ? O2 C5 C7 108.5(5) . . ? O3 C5 C7 108.2(6) . . ? O2 C5 C6 112.8(6) . . ? O3 C5 C6 108.2(4) . . ? C7 C5 C6 114.5(5) . . ? C4A C5A H5A1 109.5 . . ? C4A C5A H5A2 109.5 . . ? H5A1 C5A H5A2 109.5 . . ? C4A C5A H5A3 109.5 . . ? H5A1 C5A H5A3 109.5 . . ? H5A2 C5A H5A3 109.5 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4A C6A H6A1 109.5 . . ? C4A C6A H6A2 109.5 . . ? H6A1 C6A H6A2 109.5 . . ? C4A C6A H6A3 109.5 . . ? H6A1 C6A H6A3 109.5 . . ? H6A2 C6A H6A3 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O3A C7A C8A 108.1(3) . . ? O3A C7A C3A 102.2(3) . . ? C8A C7A C3A 116.1(3) . . ? O3A C7A H8V 110.0 . . ? C8A C7A H8V 110.0 . . ? C3A C7A H8V 110.0 . . ? O3 C8 C4 106.2(4) . . ? O3 C8 C1 107.9(4) . . ? C4 C8 C1 114.4(4) . . ? O3 C8 H8 109.4 . . ? C4 C8 H8 109.4 . . ? C1 C8 H8 109.4 . . ? N1A C8A C16A 112.1(3) . . ? N1A C8A C7A 110.2(3) . . ? C16A C8A C7A 107.2(3) . . ? N1A C8A H8A 109.1 . . ? C16A C8A H8A 109.1 . . ? C7A C8A H8A 109.1 . . ? C10 C9 N1 111.5(3) . . ? C10 C9 H9A 109.3 . . ? N1 C9 H9A 109.3 . . ? C10 C9 H9B 109.3 . . ? N1 C9 H9B 109.3 . . ? H9A C9 H9B 108.0 . . ? N1A C9A C10A 114.1(3) . . ? N1A C9A H9A1 108.7 . . ? C10A C9A H9A1 108.7 . . ? N1A C9A H9A2 108.7 . . ? C10A C9A H9A2 108.7 . . ? H9A1 C9A H9A2 107.6 . . ? C11 C10 C15 119.2(5) . . ? C11 C10 C9 119.5(5) . . ? C15 C10 C9 121.4(4) . . ? C15A C10A C11A 117.4(4) . . ? C15A C10A C9A 120.5(4) . . ? C11A C10A C9A 122.0(4) . . ? C10 C11 C12 119.4(5) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C10A C11A C12A 121.4(5) . . ? C10A C11A H11A 119.3 . . ? C12A C11A H11A 119.3 . . ? C11 C12 C13 120.9(5) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C13A C12A C11A 119.9(6) . . ? C13A C12A H12A 120.1 . . ? C11A C12A H12A 120.1 . . ? C14 C13 C12 119.0(5) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? C12A C13A C14A 120.5(5) . . ? C12A C13A H13A 119.8 . . ? C14A C13A H13A 119.8 . . ? C13 C14 C15 121.0(5) . . ? C13 C14 H14 119.5 . . ? C15 C14 H14 119.5 . . ? C13A C14A C15A 119.7(5) . . ? C13A C14A H14A 120.2 . . ? C15A C14A H14A 120.2 . . ? C10 C15 C14 120.5(5) . . ? C10 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C10A C15A C14A 121.0(5) . . ? C10A C15A H15A 119.5 . . ? C14A C15A H15A 119.5 . . ? C25 C16 C17 117.8(4) . . ? C25 C16 C1 119.9(4) . . ? C17 C16 C1 122.3(4) . . ? C25A C16A C17A 117.1(4) . . ? C25A C16A C8A 118.5(3) . . ? C17A C16A C8A 124.2(4) . . ? C22 C17 C18 116.6(6) . . ? C22 C17 C16 120.8(5) . . ? C18 C17 C16 122.6(5) . . ? C22A C17A C18A 117.4(4) . . ? C22A C17A C16A 120.7(4) . . ? C18A C17A C16A 121.8(4) . . ? C19 C18 C17 122.5(6) . . ? C19 C18 H18 118.8 . . ? C17 C18 H18 118.8 . . ? C19A C18A C17A 122.3(5) . . ? C19A C18A H18A 118.8 . . ? C17A C18A H18A 118.8 . . ? C18 C19 C20 120.4(8) . . ? C18 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? C18A C19A C20A 117.7(6) . . ? C18A C19A H19A 121.2 . . ? C20A C19A H19A 121.2 . . ? C21 C20 C19 121.4(9) . . ? C21 C20 H20 119.3 . . ? C19 C20 H20 119.3 . . ? C21A C20A C19A 122.1(5) . . ? C21A C20A H20A 119.0 . . ? C19A C20A H20A 119.0 . . ? C20 C21 C22 119.1(8) . . ? C20 C21 H21 120.4 . . ? C22 C21 H21 120.4 . . ? C20A C21A C22A 120.1(6) . . ? C20A C21A H21A 119.9 . . ? C22A C21A H21A 119.9 . . ? C17 C22 C23 118.3(6) . . ? C17 C22 C21 120.0(7) . . ? C23 C22 C21 121.7(7) . . ? C21A C22A C17A 120.3(6) . . ? C21A C22A C23A 121.3(6) . . ? C17A C22A C23A 118.3(4) . . ? C24 C23 C22 122.0(6) . . ? C24 C23 H23 119.0 . . ? C22 C23 H23 119.0 . . ? C24A C23A C22A 121.5(5) . . ? C24A C23A H23A 119.3 . . ? C22A C23A H23A 119.3 . . ? C23 C24 C25 119.6(6) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? C23A C24A C25A 119.7(5) . . ? C23A C24A H24A 120.1 . . ? C25A C24A H24A 120.1 . . ? O4 C25 C16 121.0(5) . . ? O4 C25 C24 117.6(5) . . ? C16 C25 C24 121.4(5) . . ? O4A C25A C16A 121.4(4) . . ? O4A C25A C24A 116.0(4) . . ? C16A C25A C24A 122.5(4) . . ? C2 N1 C1 110.0(3) . . ? C2 N1 C9 110.0(4) . . ? C1 N1 C9 108.4(3) . . ? C1A N1A C9A 109.0(3) . . ? C1A N1A C8A 108.8(3) . . ? C9A N1A C8A 109.9(3) . . ? C3 O1 H1B 109.5 . . ? C2A O1A H1A 109.5 . . ? C5 O2 C4 107.9(4) . . ? C4A O2A C3A 104.9(3) . . ? C8 O3 C5 108.0(4) . . ? C4A O3A C7A 108.7(3) . . ? C25 O4 H4O 109.5 . . ? C25A O4A H4A 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1A C1A C2A O1A 176.7(3) . . . . ? N1A C1A C2A C3A -58.0(4) . . . . ? N1 C2 C3 O1 178.5(4) . . . . ? N1 C2 C3 C4 -56.9(5) . . . . ? O1A C2A C3A O2A 51.4(5) . . . . ? C1A C2A C3A O2A -73.4(4) . . . . ? O1A C2A C3A C7A 166.4(4) . . . . ? C1A C2A C3A C7A 41.6(5) . . . . ? O1 C3 C4 O2 50.7(6) . . . . ? C2 C3 C4 O2 -73.5(5) . . . . ? O1 C3 C4 C8 164.6(4) . . . . ? C2 C3 C4 C8 40.4(6) . . . . ? O2A C3A C7A O3A -34.1(4) . . . . ? C2A C3A C7A O3A -154.4(3) . . . . ? O2A C3A C7A C8A 83.3(4) . . . . ? C2A C3A C7A C8A -37.0(5) . . . . ? O2 C4 C8 O3 -31.5(5) . . . . ? C3 C4 C8 O3 -152.6(4) . . . . ? O2 C4 C8 C1 87.4(5) . . . . ? C3 C4 C8 C1 -33.7(6) . . . . ? C16 C1 C8 O3 -78.9(4) . . . . ? N1 C1 C8 O3 159.4(3) . . . . ? C16 C1 C8 C4 163.1(4) . . . . ? N1 C1 C8 C4 41.5(5) . . . . ? O3A C7A C8A N1A 159.5(3) . . . . ? C3A C7A C8A N1A 45.4(4) . . . . ? O3A C7A C8A C16A -78.2(4) . . . . ? C3A C7A C8A C16A 167.7(3) . . . . ? N1 C9 C10 C11 77.5(5) . . . . ? N1 C9 C10 C15 -102.1(5) . . . . ? N1A C9A C10A C15A -128.0(4) . . . . ? N1A C9A C10A C11A 56.5(6) . . . . ? C15 C10 C11 C12 1.3(7) . . . . ? C9 C10 C11 C12 -178.4(4) . . . . ? C15A C10A C11A C12A 3.2(9) . . . . ? C9A C10A C11A C12A 179.0(5) . . . . ? C10 C11 C12 C13 0.0(8) . . . . ? C10A C11A C12A C13A -4.9(11) . . . . ? C11 C12 C13 C14 -1.1(8) . . . . ? C11A C12A C13A C14A 2.8(11) . . . . ? C12 C13 C14 C15 0.9(8) . . . . ? C12A C13A C14A C15A 0.6(10) . . . . ? C11 C10 C15 C14 -1.5(6) . . . . ? C9 C10 C15 C14 178.1(4) . . . . ? C13 C14 C15 C10 0.4(7) . . . . ? C11A C10A C15A C14A 0.3(8) . . . . ? C9A C10A C15A C14A -175.5(4) . . . . ? C13A C14A C15A C10A -2.2(9) . . . . ? N1 C1 C16 C25 47.7(5) . . . . ? C8 C1 C16 C25 -73.3(5) . . . . ? N1 C1 C16 C17 -134.4(4) . . . . ? C8 C1 C16 C17 104.6(4) . . . . ? N1A C8A C16A C25A 45.3(4) . . . . ? C7A C8A C16A C25A -75.7(4) . . . . ? N1A C8A C16A C17A -140.2(3) . . . . ? C7A C8A C16A C17A 98.8(4) . . . . ? C25 C16 C17 C22 1.0(6) . . . . ? C1 C16 C17 C22 -176.8(4) . . . . ? C25 C16 C17 C18 -179.6(4) . . . . ? C1 C16 C17 C18 2.5(6) . . . . ? C25A C16A C17A C22A 3.6(5) . . . . ? C8A C16A C17A C22A -171.0(3) . . . . ? C25A C16A C17A C18A -179.0(4) . . . . ? C8A C16A C17A C18A 6.5(6) . . . . ? C22 C17 C18 C19 -1.6(7) . . . . ? C16 C17 C18 C19 179.1(5) . . . . ? C22A C17A C18A C19A 0.3(6) . . . . ? C16A C17A C18A C19A -177.2(4) . . . . ? C17 C18 C19 C20 1.8(10) . . . . ? C17A C18A C19A C20A 0.8(7) . . . . ? C18 C19 C20 C21 -1.7(12) . . . . ? C18A C19A C20A C21A -2.4(8) . . . . ? C19 C20 C21 C22 1.4(12) . . . . ? C19A C20A C21A C22A 2.8(9) . . . . ? C18 C17 C22 C23 -179.5(4) . . . . ? C16 C17 C22 C23 -0.1(7) . . . . ? C18 C17 C22 C21 1.3(7) . . . . ? C16 C17 C22 C21 -179.4(4) . . . . ? C20 C21 C22 C17 -1.2(9) . . . . ? C20 C21 C22 C23 179.6(6) . . . . ? C20A C21A C22A C17A -1.6(7) . . . . ? C20A C21A C22A C23A 178.1(5) . . . . ? C18A C17A C22A C21A 0.0(6) . . . . ? C16A C17A C22A C21A 177.6(4) . . . . ? C18A C17A C22A C23A -179.7(4) . . . . ? C16A C17A C22A C23A -2.1(6) . . . . ? C17 C22 C23 C24 -1.8(8) . . . . ? C21 C22 C23 C24 177.4(5) . . . . ? C21A C22A C23A C24A 179.7(4) . . . . ? C17A C22A C23A C24A -0.6(7) . . . . ? C22 C23 C24 C25 2.8(8) . . . . ? C22A C23A C24A C25A 1.7(7) . . . . ? C17 C16 C25 O4 177.3(4) . . . . ? C1 C16 C25 O4 -4.7(6) . . . . ? C17 C16 C25 C24 -0.1(6) . . . . ? C1 C16 C25 C24 177.9(4) . . . . ? C23 C24 C25 O4 -179.3(5) . . . . ? C23 C24 C25 C16 -1.8(7) . . . . ? C17A C16A C25A O4A 179.3(3) . . . . ? C8A C16A C25A O4A -5.8(5) . . . . ? C17A C16A C25A C24A -2.5(5) . . . . ? C8A C16A C25A C24A 172.4(3) . . . . ? C23A C24A C25A O4A 178.2(4) . . . . ? C23A C24A C25A C16A -0.1(6) . . . . ? C3 C2 N1 C1 67.6(5) . . . . ? C3 C2 N1 C9 -173.0(4) . . . . ? C16 C1 N1 C2 -178.1(3) . . . . ? C8 C1 N1 C2 -58.3(4) . . . . ? C16 C1 N1 C9 61.5(4) . . . . ? C8 C1 N1 C9 -178.7(3) . . . . ? C10 C9 N1 C2 77.4(4) . . . . ? C10 C9 N1 C1 -162.3(4) . . . . ? C2A C1A N1A C9A -172.3(3) . . . . ? C2A C1A N1A C8A 67.9(4) . . . . ? C10A C9A N1A C1A 70.7(4) . . . . ? C10A C9A N1A C8A -170.3(3) . . . . ? C16A C8A N1A C1A -178.6(3) . . . . ? C7A C8A N1A C1A -59.2(4) . . . . ? C16A C8A N1A C9A 62.2(4) . . . . ? C7A C8A N1A C9A -178.5(3) . . . . ? O3 C5 O2 C4 -30.8(5) . . . . ? C7 C5 O2 C4 -145.9(5) . . . . ? C6 C5 O2 C4 86.3(5) . . . . ? C3 C4 O2 C5 162.6(5) . . . . ? C8 C4 O2 C5 38.2(5) . . . . ? O3A C4A O2A C3A -26.5(5) . . . . ? C5A C4A O2A C3A 91.7(4) . . . . ? C6A C4A O2A C3A -145.6(4) . . . . ? C2A C3A O2A C4A 159.3(4) . . . . ? C7A C3A O2A C4A 37.2(4) . . . . ? C4 C8 O3 C5 14.5(5) . . . . ? C1 C8 O3 C5 -108.6(4) . . . . ? O2 C5 O3 C8 9.1(5) . . . . ? C7 C5 O3 C8 124.4(5) . . . . ? C6 C5 O3 C8 -111.1(6) . . . . ? O2A C4A O3A C7A 3.8(5) . . . . ? C5A C4A O3A C7A -115.7(4) . . . . ? C6A C4A O3A C7A 121.9(4) . . . . ? C8A C7A O3A C4A -104.1(4) . . . . ? C3A C7A O3A C4A 18.9(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C3 H3 O2A 0.98 2.63 3.430(6) 138.5 2_666 C8 H8 O4 0.98 2.65 3.181(5) 114.6 . O1 H1B O1A 0.82 2.22 2.695(5) 116.9 2_666 O4 H4O N1 0.82 1.96 2.680(5) 146.6 . O4A H4A N1A 0.82 1.93 2.657(4) 147.9 . _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 22.60 _diffrn_measured_fraction_theta_full 0.950 _refine_diff_density_max 0.117 _refine_diff_density_min -0.133 _refine_diff_density_rms 0.028 _vrf_THETM01_I ; PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550 RESPONSE: The crystal was poorly diffracting at higher Bragg angles. The situation did not improve even after recrystallisation and fresh data collection. ; _vrf_PLAT023_I ; PROBLEM: Resolution (too) Low [sin(theta)/Lambda < 0.6].. 22.60 Deg. RESPONSE:The crystal was poorly diffracting at higher Bragg angles. The situation did not improve even after recrystallisation and fresh data collection. ; # end Validation Reply Form _database_code_depnum_ccdc_archive 'CCDC 931863' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_new #TrackingRef 'cpd 31.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H22 N2 O3' _chemical_formula_sum 'C18 H22 N2 O3' _chemical_formula_weight 314.38 _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.1766(4) _cell_length_b 9.1880(5) _cell_length_c 14.0208(6) _cell_angle_alpha 90.00 _cell_angle_beta 91.209(2) _cell_angle_gamma 90.00 _cell_volume 795.51(8) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Colourles _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9840 _exptl_absorpt_correction_T_max 0.9893 _exptl_absorpt_process_details 'SADABS (Bruker,2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II CCD are detector' _diffrn_measurement_method 'pi and omega scans ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5318 _diffrn_reflns_av_R_equivalents 0.0306 _diffrn_reflns_av_sigmaI/netI 0.0686 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 27.21 _reflns_number_total 3037 _reflns_number_gt 2128 _reflns_threshold_expression >2sigma(I) _computing_data_collection APEXII,Bruker,2004 _computing_cell_refinement APEXII,Bruker,2004 _computing_data_reduction SAINT,Bruker,2004 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0373P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.2(13) _refine_ls_number_reflns 3037 _refine_ls_number_parameters 218 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0824 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.0906 _refine_ls_wR_factor_gt 0.0795 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6185(5) 0.1044(3) 0.49330(19) 0.0449(8) Uani 1 1 d . . . H1 H 0.5139 0.1739 0.4780 0.054 Uiso 1 1 calc R . . C2 C 0.6577(5) -0.0104(3) 0.4337(2) 0.0486(8) Uani 1 1 d . . . H2 H 0.5790 -0.0188 0.3767 0.058 Uiso 1 1 calc R . . C3 C 0.8148(5) -0.1153(3) 0.45731(18) 0.0494(8) Uani 1 1 d . . . H3 H 0.8371 -0.1929 0.4161 0.059 Uiso 1 1 calc R . . C4 C 0.9357(5) -0.1053(3) 0.53979(18) 0.0419(8) Uani 1 1 d . . . H4 H 1.0399 -0.1754 0.5544 0.050 Uiso 1 1 calc R . . C5 C 0.9015(4) 0.0109(3) 0.60194(17) 0.0342(6) Uani 1 1 d . . . C6 C 1.0001(4) 0.0588(3) 0.69048(16) 0.0313(6) Uani 1 1 d . . . C7 C 1.1875(4) 0.0015(3) 0.74859(18) 0.0391(7) Uani 1 1 d . . . H7A H 1.2977 -0.0359 0.7068 0.047 Uiso 1 1 calc R . . H7B H 1.1398 -0.0774 0.7891 0.047 Uiso 1 1 calc R . . C8 C 1.2802(4) 0.1236(3) 0.80935(19) 0.0359(7) Uani 1 1 d . . . H8A H 1.3849 0.0836 0.8547 0.043 Uiso 1 1 calc R . . H8B H 1.3556 0.1915 0.7688 0.043 Uiso 1 1 calc R . . C9 C 1.2111(4) 0.3119(3) 0.92577(17) 0.0341(7) Uani 1 1 d . . . H9A H 1.2818 0.3858 0.8880 0.041 Uiso 1 1 calc R . . H9B H 1.3205 0.2654 0.9660 0.041 Uiso 1 1 calc R . . C10 C 1.0436(4) 0.3833(3) 0.98801(16) 0.0318(6) Uani 1 1 d . . . H10 H 0.9924 0.3099 1.0329 0.038 Uiso 1 1 calc R . . C11 C 0.8481(4) 0.4403(3) 0.93216(17) 0.0320(7) Uani 1 1 d . . . H11 H 0.7272 0.4544 0.9754 0.038 Uiso 1 1 calc R . . C12 C 0.7250(5) 0.5885(3) 0.81081(19) 0.0415(8) Uani 1 1 d . . . C13 C 0.7767(4) 0.3432(3) 0.84984(16) 0.0282(6) Uani 1 1 d . . . H13 H 0.6841 0.2643 0.8724 0.034 Uiso 1 1 calc R . . C14 C 0.9658(4) 0.2824(3) 0.79483(16) 0.0255(6) Uani 1 1 d . . . H14 H 1.0467 0.3645 0.7686 0.031 Uiso 1 1 calc R . . C15 C 0.9018(4) 0.1846(3) 0.71460(17) 0.0294(6) Uani 1 1 d . . . C16 C 0.7407(5) 0.1131(3) 0.57735(17) 0.0327(6) Uani 1 1 d . . . C17 C 0.5306(5) 0.6718(3) 0.8457(2) 0.0617(10) Uani 1 1 d . . . H17A H 0.5726 0.7699 0.8606 0.093 Uiso 1 1 calc R . . H17B H 0.4766 0.6256 0.9018 0.093 Uiso 1 1 calc R . . H17C H 0.4195 0.6727 0.7968 0.093 Uiso 1 1 calc R . . C18 C 0.8258(6) 0.6556(4) 0.7245(2) 0.0675(11) Uani 1 1 d . . . H18A H 0.9409 0.5943 0.7030 0.101 Uiso 1 1 calc R . . H18B H 0.8829 0.7497 0.7408 0.101 Uiso 1 1 calc R . . H18C H 0.7181 0.6655 0.6746 0.101 Uiso 1 1 calc R . . N1 N 0.7415(4) 0.2184(3) 0.64818(15) 0.0355(6) Uani 1 1 d . . . N2 N 1.1116(3) 0.2027(2) 0.86174(13) 0.0283(5) Uani 1 1 d . . . O1 O 1.1546(3) 0.4927(2) 1.04168(13) 0.0457(6) Uani 1 1 d . . . O2 O 0.8903(3) 0.57314(18) 0.88293(12) 0.0398(5) Uani 1 1 d . . . O3 O 0.6548(3) 0.44114(17) 0.78943(12) 0.0342(5) Uani 1 1 d . . . H1N H 1.053(5) 0.563(4) 1.075(2) 0.075(11) Uiso 1 1 d . . . H2N H 0.666(5) 0.296(3) 0.651(2) 0.057(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.049(2) 0.0493(19) 0.0363(16) -0.0047(14) -0.0117(16) 0.0002(16) C2 0.054(2) 0.057(2) 0.0341(16) -0.0115(15) -0.0111(15) -0.0058(18) C3 0.063(2) 0.0517(19) 0.0338(17) -0.0171(15) 0.0028(17) -0.0049(18) C4 0.055(2) 0.0379(16) 0.0333(15) -0.0074(13) 0.0008(15) 0.0032(15) C5 0.0425(17) 0.0343(15) 0.0256(14) -0.0026(13) 0.0012(13) -0.0052(15) C6 0.0370(17) 0.0307(14) 0.0261(14) -0.0014(11) -0.0003(13) -0.0002(13) C7 0.0414(17) 0.0369(15) 0.0390(16) -0.0059(13) -0.0016(14) 0.0093(15) C8 0.0281(16) 0.0405(15) 0.0389(15) 0.0002(13) -0.0024(13) 0.0024(14) C9 0.0328(16) 0.0386(16) 0.0302(14) -0.0019(12) -0.0115(13) -0.0007(14) C10 0.0382(17) 0.0318(14) 0.0252(13) -0.0028(12) -0.0049(13) 0.0003(13) C11 0.0345(18) 0.0317(15) 0.0295(14) -0.0014(12) -0.0044(13) -0.0004(13) C12 0.053(2) 0.0262(16) 0.0442(17) -0.0005(13) -0.0222(16) -0.0029(15) C13 0.0302(15) 0.0269(13) 0.0272(13) 0.0010(11) -0.0044(12) -0.0010(12) C14 0.0272(15) 0.0241(13) 0.0251(13) 0.0006(11) -0.0021(12) -0.0037(12) C15 0.0321(16) 0.0310(15) 0.0249(13) -0.0004(11) -0.0016(13) -0.0028(13) C16 0.0360(17) 0.0352(15) 0.0269(14) -0.0055(12) 0.0011(13) -0.0040(13) C17 0.069(2) 0.0403(18) 0.074(2) -0.0151(16) -0.0345(19) 0.0213(17) C18 0.088(3) 0.055(2) 0.058(2) 0.0207(17) -0.029(2) -0.024(2) N1 0.0415(15) 0.0314(13) 0.0332(13) -0.0035(11) -0.0069(12) 0.0074(13) N2 0.0279(12) 0.0295(12) 0.0274(11) -0.0025(10) -0.0033(10) 0.0003(10) O1 0.0427(13) 0.0510(13) 0.0429(12) -0.0202(10) -0.0130(10) 0.0061(11) O2 0.0526(13) 0.0266(10) 0.0395(11) -0.0004(8) -0.0198(10) -0.0027(10) O3 0.0398(12) 0.0276(9) 0.0347(10) -0.0025(8) -0.0118(9) 0.0018(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.370(4) . ? C1 C16 1.388(4) . ? C1 H1 0.9300 . ? C2 C3 1.402(4) . ? C2 H2 0.9300 . ? C3 C4 1.366(4) . ? C3 H3 0.9300 . ? C4 C5 1.397(3) . ? C4 H4 0.9300 . ? C5 C16 1.405(4) . ? C5 C6 1.440(3) . ? C6 C15 1.352(3) . ? C6 C7 1.497(3) . ? C7 C8 1.514(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N2 1.478(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N2 1.472(3) . ? C9 C10 1.517(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 O1 1.423(3) . ? C10 C11 1.518(3) . ? C10 H10 0.9800 . ? C11 O2 1.429(3) . ? C11 C13 1.517(3) . ? C11 H11 0.9800 . ? C12 O2 1.428(3) . ? C12 O3 1.451(3) . ? C12 C18 1.505(4) . ? C12 C17 1.514(4) . ? C13 O3 1.437(3) . ? C13 C14 1.520(3) . ? C13 H13 0.9800 . ? C14 N2 1.481(3) . ? C14 C15 1.487(3) . ? C14 H14 0.9800 . ? C15 N1 1.380(3) . ? C16 N1 1.386(3) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? N1 H2N 0.85(3) . ? O1 H1N 1.02(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C16 117.5(3) . . ? C2 C1 H1 121.3 . . ? C16 C1 H1 121.3 . . ? C1 C2 C3 121.1(3) . . ? C1 C2 H2 119.5 . . ? C3 C2 H2 119.5 . . ? C4 C3 C2 121.1(3) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 119.5(3) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C4 C5 C16 118.2(2) . . ? C4 C5 C6 134.8(3) . . ? C16 C5 C6 106.9(2) . . ? C15 C6 C5 107.0(2) . . ? C15 C6 C7 120.7(2) . . ? C5 C6 C7 132.0(2) . . ? C6 C7 C8 108.9(2) . . ? C6 C7 H7A 109.9 . . ? C8 C7 H7A 109.9 . . ? C6 C7 H7B 109.9 . . ? C8 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? N2 C8 C7 112.4(2) . . ? N2 C8 H8A 109.1 . . ? C7 C8 H8A 109.1 . . ? N2 C8 H8B 109.1 . . ? C7 C8 H8B 109.1 . . ? H8A C8 H8B 107.8 . . ? N2 C9 C10 111.39(19) . . ? N2 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? N2 C9 H9B 109.4 . . ? C10 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? O1 C10 C9 106.4(2) . . ? O1 C10 C11 113.5(2) . . ? C9 C10 C11 113.4(2) . . ? O1 C10 H10 107.7 . . ? C9 C10 H10 107.7 . . ? C11 C10 H10 107.7 . . ? O2 C11 C13 100.83(18) . . ? O2 C11 C10 113.1(2) . . ? C13 C11 C10 113.9(2) . . ? O2 C11 H11 109.6 . . ? C13 C11 H11 109.6 . . ? C10 C11 H11 109.6 . . ? O2 C12 O3 105.09(19) . . ? O2 C12 C18 107.9(2) . . ? O3 C12 C18 110.1(2) . . ? O2 C12 C17 112.4(2) . . ? O3 C12 C17 107.6(2) . . ? C18 C12 C17 113.4(3) . . ? O3 C13 C11 102.74(19) . . ? O3 C13 C14 109.24(19) . . ? C11 C13 C14 112.8(2) . . ? O3 C13 H13 110.6 . . ? C11 C13 H13 110.6 . . ? C14 C13 H13 110.6 . . ? N2 C14 C15 109.17(19) . . ? N2 C14 C13 108.91(18) . . ? C15 C14 C13 114.27(19) . . ? N2 C14 H14 108.1 . . ? C15 C14 H14 108.1 . . ? C13 C14 H14 108.1 . . ? C6 C15 N1 110.1(2) . . ? C6 C15 C14 126.3(2) . . ? N1 C15 C14 123.4(2) . . ? N1 C16 C1 129.9(3) . . ? N1 C16 C5 107.4(2) . . ? C1 C16 C5 122.6(2) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C12 C18 H18A 109.5 . . ? C12 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C12 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C15 N1 C16 108.6(2) . . ? C15 N1 H2N 123(2) . . ? C16 N1 H2N 128(2) . . ? C9 N2 C8 110.40(18) . . ? C9 N2 C14 106.82(18) . . ? C8 N2 C14 110.72(18) . . ? C10 O1 H1N 113.4(18) . . ? C12 O2 C11 106.93(19) . . ? C13 O3 C12 108.16(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 C1 C2 C3 0.3(4) . . . . ? C1 C2 C3 C4 -0.9(5) . . . . ? C2 C3 C4 C5 0.3(4) . . . . ? C3 C4 C5 C16 0.7(4) . . . . ? C3 C4 C5 C6 -177.2(3) . . . . ? C4 C5 C6 C15 177.1(3) . . . . ? C16 C5 C6 C15 -0.9(3) . . . . ? C4 C5 C6 C7 2.4(5) . . . . ? C16 C5 C6 C7 -175.6(3) . . . . ? C15 C6 C7 C8 -18.0(3) . . . . ? C5 C6 C7 C8 156.2(3) . . . . ? C6 C7 C8 N2 49.2(3) . . . . ? N2 C9 C10 O1 -176.16(18) . . . . ? N2 C9 C10 C11 -50.7(3) . . . . ? O1 C10 C11 O2 45.2(3) . . . . ? C9 C10 C11 O2 -76.5(3) . . . . ? O1 C10 C11 C13 159.5(2) . . . . ? C9 C10 C11 C13 37.9(3) . . . . ? O2 C11 C13 O3 -37.3(2) . . . . ? C10 C11 C13 O3 -158.7(2) . . . . ? O2 C11 C13 C14 80.2(2) . . . . ? C10 C11 C13 C14 -41.2(3) . . . . ? O3 C13 C14 N2 170.21(18) . . . . ? C11 C13 C14 N2 56.6(2) . . . . ? O3 C13 C14 C15 -67.4(2) . . . . ? C11 C13 C14 C15 179.0(2) . . . . ? C5 C6 C15 N1 1.6(3) . . . . ? C7 C6 C15 N1 177.1(2) . . . . ? C5 C6 C15 C14 -172.8(2) . . . . ? C7 C6 C15 C14 2.6(4) . . . . ? N2 C14 C15 C6 -16.5(3) . . . . ? C13 C14 C15 C6 -138.7(2) . . . . ? N2 C14 C15 N1 169.7(2) . . . . ? C13 C14 C15 N1 47.5(3) . . . . ? C2 C1 C16 N1 177.3(3) . . . . ? C2 C1 C16 C5 0.8(4) . . . . ? C4 C5 C16 N1 -178.5(2) . . . . ? C6 C5 C16 N1 -0.1(3) . . . . ? C4 C5 C16 C1 -1.3(4) . . . . ? C6 C5 C16 C1 177.1(2) . . . . ? C6 C15 N1 C16 -1.8(3) . . . . ? C14 C15 N1 C16 172.9(2) . . . . ? C1 C16 N1 C15 -175.8(3) . . . . ? C5 C16 N1 C15 1.1(3) . . . . ? C10 C9 N2 C8 -174.0(2) . . . . ? C10 C9 N2 C14 65.6(2) . . . . ? C7 C8 N2 C9 175.3(2) . . . . ? C7 C8 N2 C14 -66.7(3) . . . . ? C15 C14 N2 C9 166.54(19) . . . . ? C13 C14 N2 C9 -68.1(2) . . . . ? C15 C14 N2 C8 46.3(2) . . . . ? C13 C14 N2 C8 171.69(19) . . . . ? O3 C12 O2 C11 -26.1(3) . . . . ? C18 C12 O2 C11 -143.5(2) . . . . ? C17 C12 O2 C11 90.7(2) . . . . ? C13 C11 O2 C12 39.3(3) . . . . ? C10 C11 O2 C12 161.3(2) . . . . ? C11 C13 O3 C12 22.6(2) . . . . ? C14 C13 O3 C12 -97.4(2) . . . . ? O2 C12 O3 C13 0.9(3) . . . . ? C18 C12 O3 C13 116.8(2) . . . . ? C17 C12 O3 C13 -119.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.918 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.945 _refine_diff_density_max 0.141 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.038 _database_code_depnum_ccdc_archive 'CCDC 931864' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl2 #TrackingRef 'new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C63 H75 N3 O15' _chemical_formula_weight 1114.26 _chemical_absolute_configuration rm loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 10.1384(5) _cell_length_b 10.2329(5) _cell_length_c 14.4261(6) _cell_angle_alpha 87.321(2) _cell_angle_beta 89.563(2) _cell_angle_gamma 79.123(2) _cell_volume 1468.14(12) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5892 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 27.20 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 594 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9036 _exptl_absorpt_correction_T_max 0.9779 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD Diffractometer' _diffrn_measurement_method '\w and \f scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19662 _diffrn_reflns_av_R_equivalents 0.0152 _diffrn_reflns_av_sigmaI/netI 0.0249 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 33.04 _reflns_number_total 10814 _reflns_number_gt 9419 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEXII, Bruker,2004' _computing_cell_refinement 'APEXII/SAINT, Bruker,2004' _computing_data_reduction 'SAINT PLUS/XPREP, Bruker,2004' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0409P)^2^+0.1534P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.5(5) _refine_ls_number_reflns 10814 _refine_ls_number_parameters 755 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0411 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0813 _refine_ls_wR_factor_gt 0.0768 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1A C 0.06953(15) 0.72889(17) 0.42517(12) 0.0361(4) Uani 1 1 d . . . H1A H 0.1283 0.7934 0.4330 0.043 Uiso 1 1 calc R . . C2A C 0.14235(16) 0.58888(17) 0.45951(12) 0.0371(4) Uani 1 1 d . . . H2A H 0.0755 0.5341 0.4763 0.044 Uiso 1 1 calc R . . C3A C 0.15825(19) 0.51810(19) 0.30060(13) 0.0468(4) Uani 1 1 d . . . H3A1 H 0.0849 0.4712 0.3132 0.056 Uiso 1 1 calc R . . H3A2 H 0.2175 0.4686 0.2560 0.056 Uiso 1 1 calc R . . C4A C 0.10257(19) 0.6552(2) 0.25915(13) 0.0476(5) Uani 1 1 d . . . H4A H 0.0487 0.6470 0.2044 0.057 Uiso 1 1 calc R . . C5A C 0.01605(17) 0.74192(19) 0.32742(13) 0.0416(4) Uani 1 1 d . . . H5A H 0.0023 0.8354 0.3049 0.050 Uiso 1 1 calc R . . C6A C -0.16511(17) 0.7557(2) 0.42245(13) 0.0468(4) Uani 1 1 d . . . C7A C -0.2438(2) 0.6604(3) 0.46812(18) 0.0748(7) Uani 1 1 d . . . H7A1 H -0.3181 0.6528 0.4292 0.112 Uiso 1 1 calc R . . H7A2 H -0.2768 0.6927 0.5269 0.112 Uiso 1 1 calc R . . H7A3 H -0.1868 0.5745 0.4775 0.112 Uiso 1 1 calc R . . C8A C -0.2467(2) 0.8948(3) 0.40673(18) 0.0751(7) Uani 1 1 d . . . H8A1 H -0.1924 0.9507 0.3758 0.113 Uiso 1 1 calc R . . H8A2 H -0.2761 0.9305 0.4654 0.113 Uiso 1 1 calc R . . H8A3 H -0.3236 0.8915 0.3690 0.113 Uiso 1 1 calc R . . C9A C 0.22272(16) 0.60445(17) 0.54432(12) 0.0377(4) Uani 1 1 d . . . C10A C 0.17828(16) 0.58172(17) 0.63332(13) 0.0408(4) Uani 1 1 d . . . H10A H 0.0992 0.5490 0.6416 0.049 Uiso 1 1 calc R . . C11A C 0.24854(18) 0.60651(19) 0.71082(14) 0.0463(5) Uani 1 1 d . . . H11A H 0.2164 0.5915 0.7702 0.056 Uiso 1 1 calc R . . C12A C 0.36710(19) 0.65381(18) 0.69856(14) 0.0454(4) Uani 1 1 d . . . C13A C 0.41331(18) 0.67703(18) 0.61052(14) 0.0451(4) Uani 1 1 d . . . H13A H 0.4929 0.7090 0.6028 0.054 Uiso 1 1 calc R . . C14A C 0.34311(16) 0.65353(17) 0.53381(13) 0.0397(4) Uani 1 1 d . . . C15A C 0.29715(9) 0.38674(9) 0.42035(8) 0.0503(5) Uani 1 1 d D . . H15A H 0.2357 0.3258 0.4130 0.060 Uiso 1 1 calc R A 1 H15B H 0.3186 0.3868 0.4858 0.060 Uiso 1 1 calc R A 1 C16A C 0.42978(9) 0.33915(9) 0.36328(8) 0.0398(5) Uani 0.476(3) 1 d PRD B 1 C17A C 0.54565(9) 0.38839(9) 0.38014(8) 0.0672(13) Uani 0.476(3) 1 d PR B 1 H17A H 0.5427 0.4583 0.4195 0.081 Uiso 0.476(3) 1 calc PR B 1 C18A C 0.66585(9) 0.33312(9) 0.33818(8) 0.0836(18) Uani 0.476(3) 1 d PR B 1 H18A H 0.7434 0.3661 0.3495 0.100 Uiso 0.476(3) 1 calc PR B 1 C19A C 0.67019(9) 0.22861(9) 0.27936(8) 0.0630(11) Uani 0.476(3) 1 d PR B 1 H19A H 0.7506 0.1916 0.2513 0.076 Uiso 0.476(3) 1 calc PR B 1 C20A C 0.55433(9) 0.17938(9) 0.26249(8) 0.0548(8) Uani 0.476(3) 1 d PR B 1 H20A H 0.5572 0.1095 0.2231 0.066 Uiso 0.476(3) 1 calc PR B 1 C21A C 0.43412(9) 0.23465(9) 0.30445(8) 0.0484(5) Uani 0.476(3) 1 d PR B 1 H21A H 0.3566 0.2017 0.2932 0.058 Uiso 0.476(3) 1 calc PR B 1 C16D C 0.43224(9) 0.33325(9) 0.38381(8) 0.0398(5) Uani 0.524(3) 1 d PRD B 2 C17D C 0.54327(9) 0.36920(9) 0.42440(8) 0.0672(13) Uani 0.524(3) 1 d PR B 2 H17D H 0.5322 0.4221 0.4756 0.081 Uiso 0.524(3) 1 calc PR B 2 C18D C 0.67083(9) 0.32605(9) 0.38846(8) 0.0836(18) Uani 0.524(3) 1 d PR B 2 H18D H 0.7451 0.3501 0.4156 0.100 Uiso 0.524(3) 1 calc PR B 2 C19D C 0.68736(9) 0.24693(9) 0.31192(8) 0.0630(11) Uani 0.524(3) 1 d PR B 2 H19D H 0.7727 0.2181 0.2879 0.076 Uiso 0.524(3) 1 calc PR B 2 C20D C 0.57632(9) 0.21098(9) 0.27133(8) 0.0548(8) Uani 0.524(3) 1 d PR B 2 H20D H 0.5874 0.1580 0.2201 0.066 Uiso 0.524(3) 1 calc PR B 2 C21D C 0.44876(9) 0.25413(9) 0.30727(8) 0.0484(5) Uani 0.524(3) 1 d PR B 2 H21D H 0.3745 0.2301 0.2801 0.058 Uiso 0.524(3) 1 calc PR B 2 C1B C 0.47874(16) 0.47852(17) 1.08993(12) 0.0364(4) Uani 1 1 d . . . H1B H 0.4771 0.4073 1.1375 0.044 Uiso 1 1 calc R . . C2B C 0.39510(15) 0.45679(17) 1.00507(12) 0.0352(4) Uani 1 1 d . . . H2B H 0.3682 0.5414 0.9694 0.042 Uiso 1 1 calc R . . C3B C 0.59789(16) 0.40285(18) 0.91400(12) 0.0400(4) Uani 1 1 d . . . H3B1 H 0.5735 0.4902 0.8830 0.048 Uiso 1 1 calc R . . H3B2 H 0.6444 0.3424 0.8694 0.048 Uiso 1 1 calc R . . C4B C 0.69062(16) 0.41051(18) 0.99279(13) 0.0405(4) Uani 1 1 d . . . H4B H 0.7661 0.4497 0.9693 0.049 Uiso 1 1 calc R . . C5B C 0.62304(16) 0.49308(18) 1.06994(13) 0.0389(4) Uani 1 1 d . . . H5B H 0.6767 0.4723 1.1268 0.047 Uiso 1 1 calc R . . C6B C 0.50922(19) 0.69933(19) 1.10447(16) 0.0525(5) Uani 1 1 d . . . C7B C 0.5684(3) 0.7320(3) 1.1932(2) 0.0842(8) Uani 1 1 d . . . H7B1 H 0.6161 0.6516 1.2237 0.126 Uiso 1 1 calc R . . H7B2 H 0.4978 0.7734 1.2329 0.126 Uiso 1 1 calc R . . H7B3 H 0.6292 0.7918 1.1801 0.126 Uiso 1 1 calc R . . C8B C 0.4306(3) 0.8189(2) 1.0516(2) 0.0884(9) Uani 1 1 d . . . H8B1 H 0.4881 0.8815 1.0370 0.133 Uiso 1 1 calc R . . H8B2 H 0.3569 0.8601 1.0889 0.133 Uiso 1 1 calc R . . H8B3 H 0.3967 0.7913 0.9953 0.133 Uiso 1 1 calc R . . C9B C 0.27155(16) 0.40766(18) 1.03946(12) 0.0389(4) Uani 1 1 d . . . C10B C 0.14435(17) 0.4870(2) 1.03876(14) 0.0455(4) Uani 1 1 d . . . H10B H 0.1325 0.5731 1.0124 0.055 Uiso 1 1 calc R . . C11B C 0.03370(18) 0.4405(2) 1.07680(15) 0.0542(5) Uani 1 1 d . . . H11B H -0.0510 0.4947 1.0751 0.065 Uiso 1 1 calc R . . C12B C 0.05172(19) 0.3129(2) 1.11708(13) 0.0543(5) Uani 1 1 d . . . C13B C 0.1760(2) 0.2320(2) 1.11752(14) 0.0523(5) Uani 1 1 d . . . H13B H 0.1871 0.1463 1.1445 0.063 Uiso 1 1 calc R . . C14B C 0.28492(17) 0.27685(19) 1.07808(13) 0.0424(4) Uani 1 1 d . . . C15B C 0.39332(18) 0.34038(19) 0.86295(13) 0.0439(4) Uani 1 1 d . . . H15C H 0.3849 0.4200 0.8226 0.053 Uiso 1 1 calc R . . H15D H 0.3039 0.3327 0.8840 0.053 Uiso 1 1 calc R . . C16B C 0.44870(18) 0.22200(18) 0.80762(13) 0.0425(4) Uani 1 1 d . . . C17B C 0.4818(2) 0.2375(2) 0.71580(15) 0.0548(5) Uani 1 1 d . . . H17B H 0.4746 0.3227 0.6885 0.066 Uiso 1 1 calc R . . C18B C 0.5260(2) 0.1270(3) 0.66299(18) 0.0697(7) Uani 1 1 d . . . H18B H 0.5479 0.1383 0.6008 0.084 Uiso 1 1 calc R . . C19B C 0.5367(3) 0.0021(3) 0.7033(2) 0.0817(9) Uani 1 1 d . . . H19B H 0.5648 -0.0720 0.6681 0.098 Uiso 1 1 calc R . . C20B C 0.5072(4) -0.0145(3) 0.7930(2) 0.0942(10) Uani 1 1 d . . . H20B H 0.5166 -0.1000 0.8202 0.113 Uiso 1 1 calc R . . C21B C 0.4627(3) 0.0945(2) 0.84558(18) 0.0734(7) Uani 1 1 d . . . H21B H 0.4418 0.0814 0.9078 0.088 Uiso 1 1 calc R . . C1C C 0.87267(17) 0.06633(16) 0.81841(12) 0.0359(4) Uani 1 1 d . . . H1C H 0.7841 0.1052 0.7924 0.043 Uiso 1 1 calc R . . C2C C 0.98053(16) 0.13573(16) 0.77184(12) 0.0360(4) Uani 1 1 d . . . H2C H 1.0589 0.1252 0.8128 0.043 Uiso 1 1 calc R . . C3C C 1.07658(17) -0.06681(16) 0.69675(13) 0.0406(4) Uani 1 1 d . . . H3C1 H 1.1484 -0.0787 0.7421 0.049 Uiso 1 1 calc R . . H3C2 H 1.1144 -0.1020 0.6391 0.049 Uiso 1 1 calc R . . C4C C 0.97140(17) -0.14396(17) 0.73012(13) 0.0392(4) Uani 1 1 d . . . H4C H 1.0159 -0.2355 0.7470 0.047 Uiso 1 1 calc R . . C5C C 0.89651(17) -0.08507(17) 0.81407(12) 0.0377(4) Uani 1 1 d . . . H5C H 0.8105 -0.1153 0.8197 0.045 Uiso 1 1 calc R . . C6C C 0.9231(2) -0.04147(19) 0.96502(14) 0.0496(5) Uani 1 1 d . . . C7C C 1.0364(3) -0.0267(3) 1.0284(2) 0.0894(9) Uani 1 1 d . . . H7C1 H 1.0770 -0.1126 1.0548 0.134 Uiso 1 1 calc R . . H7C2 H 1.0019 0.0309 1.0771 0.134 Uiso 1 1 calc R . . H7C3 H 1.1023 0.0109 0.9936 0.134 Uiso 1 1 calc R . . C8C C 0.8077(3) -0.0868(3) 1.01586(18) 0.0810(8) Uani 1 1 d . . . H8C1 H 0.7397 -0.0964 0.9721 0.122 Uiso 1 1 calc R . . H8C2 H 0.7705 -0.0219 1.0596 0.122 Uiso 1 1 calc R . . H8C3 H 0.8395 -0.1708 1.0482 0.122 Uiso 1 1 calc R . . C9C C 0.92044(16) 0.28348(16) 0.75678(12) 0.0343(4) Uani 1 1 d . . . C10C C 0.95290(17) 0.37955(17) 0.81221(13) 0.0389(4) Uani 1 1 d . . . H10C H 1.0193 0.3550 0.8572 0.047 Uiso 1 1 calc R . . C11C C 0.88821(17) 0.51245(17) 0.80215(13) 0.0413(4) Uani 1 1 d . . . H11C H 0.9115 0.5761 0.8396 0.050 Uiso 1 1 calc R . . C12C C 0.78895(16) 0.54779(16) 0.73564(13) 0.0387(4) Uani 1 1 d . . . C13C C 0.75616(17) 0.45439(17) 0.67859(13) 0.0400(4) Uani 1 1 d . . . H13C H 0.6892 0.4793 0.6340 0.048 Uiso 1 1 calc R . . C14C C 0.82311(16) 0.32328(16) 0.68775(12) 0.0356(4) Uani 1 1 d . . . C15C C 1.12390(18) 0.14277(19) 0.63478(14) 0.0446(4) Uani 1 1 d . . . H15E H 1.2084 0.1184 0.6680 0.054 Uiso 1 1 calc R . . H15F H 1.0951 0.2385 0.6366 0.054 Uiso 1 1 calc R . . C16C C 1.14501(18) 0.10514(18) 0.53539(13) 0.0438(4) Uani 1 1 d . . . C17C C 1.0473(2) 0.1466(3) 0.46927(16) 0.0661(6) Uani 1 1 d . . . H17C H 0.9661 0.1989 0.4859 0.079 Uiso 1 1 calc R . . C18C C 1.0692(3) 0.1110(3) 0.37740(18) 0.0830(9) Uani 1 1 d . . . H18C H 1.0024 0.1397 0.3332 0.100 Uiso 1 1 calc R . . C19C C 1.1881(3) 0.0342(3) 0.35219(19) 0.0787(8) Uani 1 1 d . . . H19C H 1.2018 0.0095 0.2911 0.094 Uiso 1 1 calc R . . C20C C 1.2854(3) -0.0056(2) 0.41617(18) 0.0700(7) Uani 1 1 d . . . H20C H 1.3671 -0.0563 0.3989 0.084 Uiso 1 1 calc R . . C21C C 1.2643(2) 0.0287(2) 0.50712(15) 0.0544(5) Uani 1 1 d . . . H21C H 1.3321 -0.0004 0.5505 0.065 Uiso 1 1 calc R . . N1A N 0.23253(14) 0.52308(14) 0.38672(10) 0.0406(3) Uani 1 1 d . B . N1B N 0.47526(13) 0.35691(14) 0.94464(10) 0.0355(3) Uani 1 1 d . . . N1C N 1.02189(13) 0.07594(13) 0.68184(10) 0.0365(3) Uani 1 1 d . . . O1A O 0.20482(16) 0.72715(16) 0.23314(12) 0.0656(5) Uani 1 1 d . . . O2A O -0.11039(12) 0.70186(14) 0.33885(9) 0.0486(3) Uani 1 1 d . . . O3A O -0.05070(11) 0.76510(13) 0.47950(8) 0.0438(3) Uani 1 1 d . . . O4A O 0.43641(18) 0.67454(15) 0.77608(11) 0.0616(4) Uani 1 1 d . . . O5A O 0.39291(13) 0.67951(14) 0.44865(10) 0.0500(3) Uani 1 1 d . . . O1B O 0.74214(12) 0.28193(14) 1.03541(10) 0.0491(3) Uani 1 1 d D . . O2B O 0.60921(12) 0.63119(12) 1.04485(10) 0.0497(3) Uani 1 1 d . . . O3B O 0.42177(12) 0.60529(13) 1.12602(10) 0.0478(3) Uani 1 1 d . . . O4B O -0.05152(16) 0.2632(2) 1.15879(11) 0.0770(5) Uani 1 1 d D . . O5B O 0.40411(14) 0.18943(13) 1.07698(11) 0.0525(3) Uani 1 1 d . . . O1C O 0.87154(13) -0.14840(13) 0.66125(10) 0.0460(3) Uani 1 1 d . . . O2C O 0.97546(13) -0.12879(12) 0.89453(9) 0.0485(3) Uani 1 1 d . . . O3C O 0.87251(13) 0.08461(12) 0.91639(9) 0.0471(3) Uani 1 1 d . . . O4C O 0.78996(14) 0.23667(14) 0.62727(10) 0.0484(3) Uani 1 1 d . . . O5C O 0.71472(13) 0.67662(13) 0.72709(11) 0.0532(4) Uani 1 1 d . . . H6X H 0.906(2) -0.172(2) 0.6105(18) 0.066(7) Uiso 1 1 d . . . H1X H 0.257(3) 0.686(3) 0.2018(18) 0.068(7) Uiso 1 1 d . . . H4X H 0.774(2) 0.231(2) 0.9958(14) 0.074(8) Uiso 1 1 d D . . H3X H 0.764(3) 0.724(3) 0.7027(19) 0.076(8) Uiso 1 1 d . . . H2X H 0.344(3) 0.642(3) 0.4070(19) 0.074(8) Uiso 1 1 d . . . H5X H 0.848(2) 0.169(3) 0.6338(16) 0.063(7) Uiso 1 1 d . . . H8X H 0.459(2) 0.227(2) 1.0390(16) 0.060(6) Uiso 1 1 d . . . H7X H -0.1203(19) 0.275(3) 1.1248(17) 0.091(9) Uiso 1 1 d D . . H9X H 0.529(4) 0.688(4) 0.770(2) 0.125(13) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1A 0.0284(8) 0.0381(9) 0.0417(9) -0.0075(7) 0.0075(7) -0.0053(7) C2A 0.0311(8) 0.0376(9) 0.0438(10) -0.0044(8) 0.0077(7) -0.0095(7) C3A 0.0479(10) 0.0469(11) 0.0459(11) -0.0123(9) 0.0098(8) -0.0075(8) C4A 0.0485(11) 0.0523(12) 0.0406(10) -0.0065(9) 0.0108(8) -0.0056(9) C5A 0.0354(9) 0.0445(10) 0.0431(10) -0.0021(8) 0.0072(7) -0.0029(7) C6A 0.0312(9) 0.0656(13) 0.0427(10) -0.0061(9) 0.0046(7) -0.0062(8) C7A 0.0564(14) 0.108(2) 0.0688(15) -0.0050(14) 0.0137(11) -0.0381(13) C8A 0.0573(14) 0.0854(18) 0.0698(15) -0.0082(13) -0.0033(11) 0.0205(12) C9A 0.0321(8) 0.0325(9) 0.0467(10) -0.0023(8) 0.0042(7) -0.0016(7) C10A 0.0310(8) 0.0383(10) 0.0488(11) 0.0023(8) 0.0037(7) 0.0029(7) C11A 0.0453(10) 0.0430(10) 0.0430(10) 0.0043(8) 0.0033(8) 0.0096(8) C12A 0.0455(10) 0.0337(9) 0.0523(12) -0.0036(8) -0.0122(8) 0.0058(8) C13A 0.0371(9) 0.0364(10) 0.0609(12) 0.0001(9) -0.0050(8) -0.0055(7) C14A 0.0334(9) 0.0338(9) 0.0496(11) -0.0011(8) 0.0019(7) -0.0012(7) C15A 0.0537(11) 0.0381(10) 0.0567(12) -0.0039(9) 0.0103(9) -0.0025(8) C16A 0.0436(10) 0.0326(10) 0.0403(13) 0.0041(9) -0.0013(9) -0.0011(8) C17A 0.0555(15) 0.0596(18) 0.084(4) -0.022(2) -0.0167(19) 0.0004(13) C18A 0.0431(14) 0.078(2) 0.129(6) -0.027(3) -0.016(2) -0.0054(14) C19A 0.0406(14) 0.0676(19) 0.075(3) 0.0075(19) 0.0032(16) 0.0013(13) C20A 0.0536(15) 0.0532(18) 0.0536(14) -0.0085(13) 0.0017(11) 0.0013(13) C21A 0.0429(11) 0.0446(13) 0.0569(13) -0.0045(10) 0.0006(9) -0.0057(9) C16D 0.0436(10) 0.0326(10) 0.0403(13) 0.0041(9) -0.0013(9) -0.0011(8) C17D 0.0555(15) 0.0596(18) 0.084(4) -0.022(2) -0.0167(19) 0.0004(13) C18D 0.0431(14) 0.078(2) 0.129(6) -0.027(3) -0.016(2) -0.0054(14) C19D 0.0406(14) 0.0676(19) 0.075(3) 0.0075(19) 0.0032(16) 0.0013(13) C20D 0.0536(15) 0.0532(18) 0.0536(14) -0.0085(13) 0.0017(11) 0.0013(13) C21D 0.0429(11) 0.0446(13) 0.0569(13) -0.0045(10) 0.0006(9) -0.0057(9) C1B 0.0350(8) 0.0338(9) 0.0413(9) -0.0075(7) 0.0110(7) -0.0081(7) C2B 0.0317(8) 0.0325(9) 0.0402(9) -0.0034(7) 0.0061(7) -0.0025(6) C3B 0.0380(9) 0.0425(10) 0.0377(9) -0.0033(8) 0.0102(7) -0.0033(7) C4B 0.0306(8) 0.0446(10) 0.0465(10) -0.0060(8) 0.0107(7) -0.0068(7) C5B 0.0328(8) 0.0411(10) 0.0444(10) -0.0088(8) 0.0066(7) -0.0097(7) C6B 0.0490(11) 0.0420(11) 0.0701(14) -0.0165(10) 0.0223(10) -0.0157(9) C7B 0.0728(16) 0.096(2) 0.097(2) -0.0557(17) 0.0202(14) -0.0368(14) C8B 0.0865(18) 0.0458(13) 0.129(3) 0.0018(14) 0.0305(17) -0.0039(12) C9B 0.0329(8) 0.0429(10) 0.0424(10) -0.0092(8) 0.0034(7) -0.0097(7) C10B 0.0364(9) 0.0501(11) 0.0502(11) -0.0132(9) 0.0014(8) -0.0060(8) C11B 0.0294(9) 0.0777(15) 0.0572(12) -0.0221(11) 0.0004(8) -0.0096(9) C12B 0.0407(11) 0.0883(17) 0.0414(11) -0.0053(11) -0.0005(8) -0.0306(11) C13B 0.0510(11) 0.0666(14) 0.0455(11) 0.0026(10) -0.0057(8) -0.0277(10) C14B 0.0405(10) 0.0473(11) 0.0420(10) -0.0030(8) -0.0010(8) -0.0150(8) C15B 0.0418(10) 0.0444(10) 0.0415(10) -0.0035(8) -0.0048(8) 0.0025(8) C16B 0.0404(9) 0.0403(10) 0.0473(11) -0.0071(8) -0.0081(8) -0.0073(7) C17B 0.0579(12) 0.0531(12) 0.0576(13) -0.0147(10) 0.0043(10) -0.0182(10) C18B 0.0540(13) 0.094(2) 0.0670(15) -0.0386(14) 0.0110(11) -0.0209(12) C19B 0.0720(16) 0.0618(17) 0.108(2) -0.0446(16) -0.0261(15) 0.0074(12) C20B 0.149(3) 0.0419(14) 0.087(2) -0.0143(14) -0.033(2) -0.0029(15) C21B 0.116(2) 0.0437(13) 0.0604(14) -0.0038(11) -0.0145(14) -0.0133(13) C1C 0.0371(8) 0.0304(8) 0.0390(9) -0.0029(7) 0.0054(7) -0.0036(7) C2C 0.0329(8) 0.0292(9) 0.0451(10) -0.0037(7) 0.0019(7) -0.0033(6) C3C 0.0365(9) 0.0309(9) 0.0522(11) -0.0057(8) 0.0112(8) 0.0000(7) C4C 0.0448(9) 0.0250(8) 0.0464(10) -0.0039(7) 0.0099(8) -0.0028(7) C5C 0.0418(9) 0.0295(9) 0.0422(10) -0.0028(7) 0.0073(7) -0.0074(7) C6C 0.0652(12) 0.0384(10) 0.0440(11) -0.0019(9) 0.0005(9) -0.0069(9) C7C 0.100(2) 0.087(2) 0.0762(18) -0.0118(15) -0.0293(16) -0.0011(16) C8C 0.113(2) 0.0685(16) 0.0656(16) -0.0017(13) 0.0361(15) -0.0288(15) C9C 0.0350(8) 0.0276(8) 0.0412(10) -0.0035(7) 0.0044(7) -0.0076(6) C10C 0.0370(9) 0.0367(10) 0.0437(10) -0.0026(8) 0.0030(7) -0.0087(7) C11C 0.0442(10) 0.0309(9) 0.0519(11) -0.0098(8) 0.0079(8) -0.0133(7) C12C 0.0373(9) 0.0252(8) 0.0536(11) -0.0016(8) 0.0135(8) -0.0064(7) C13C 0.0365(9) 0.0333(9) 0.0487(11) 0.0010(8) 0.0021(7) -0.0036(7) C14C 0.0359(9) 0.0302(9) 0.0425(10) -0.0067(8) 0.0048(7) -0.0094(7) C15C 0.0400(9) 0.0386(10) 0.0577(12) -0.0046(9) 0.0108(8) -0.0135(7) C16C 0.0434(10) 0.0384(10) 0.0521(11) 0.0044(8) 0.0092(8) -0.0163(8) C17C 0.0502(12) 0.0863(17) 0.0624(15) 0.0185(13) 0.0039(10) -0.0198(11) C18C 0.0852(19) 0.115(2) 0.0583(16) 0.0255(16) -0.0152(14) -0.0485(18) C19C 0.117(2) 0.0787(18) 0.0542(15) -0.0039(13) 0.0201(16) -0.0530(17) C20C 0.0926(18) 0.0518(13) 0.0658(16) -0.0027(12) 0.0282(14) -0.0150(12) C21C 0.0576(12) 0.0452(11) 0.0585(13) 0.0024(10) 0.0123(10) -0.0065(9) N1A 0.0398(8) 0.0355(8) 0.0453(9) -0.0062(7) 0.0078(6) -0.0029(6) N1B 0.0336(7) 0.0359(7) 0.0359(7) -0.0052(6) 0.0025(6) -0.0028(6) N1C 0.0362(7) 0.0262(7) 0.0473(8) -0.0026(6) 0.0108(6) -0.0069(5) O1A 0.0649(9) 0.0547(9) 0.0736(11) -0.0023(8) 0.0402(8) -0.0038(7) O2A 0.0357(6) 0.0684(9) 0.0428(7) -0.0110(6) 0.0024(5) -0.0108(6) O3A 0.0310(6) 0.0584(8) 0.0401(7) -0.0112(6) 0.0049(5) -0.0018(5) O4A 0.0666(10) 0.0575(9) 0.0588(9) -0.0017(7) -0.0192(8) -0.0063(7) O5A 0.0430(7) 0.0562(8) 0.0539(8) -0.0018(7) 0.0105(6) -0.0179(6) O1B 0.0419(7) 0.0516(8) 0.0493(8) -0.0121(7) -0.0008(6) 0.0054(6) O2B 0.0463(7) 0.0413(7) 0.0656(9) -0.0123(6) 0.0217(6) -0.0175(6) O3B 0.0427(7) 0.0427(7) 0.0618(8) -0.0218(6) 0.0225(6) -0.0137(5) O4B 0.0474(9) 0.1365(17) 0.0568(10) 0.0111(10) -0.0013(7) -0.0458(10) O5B 0.0496(8) 0.0431(8) 0.0635(9) 0.0054(7) 0.0035(7) -0.0075(6) O1C 0.0503(8) 0.0456(7) 0.0451(8) -0.0125(6) 0.0119(6) -0.0147(6) O2C 0.0597(8) 0.0341(7) 0.0481(8) 0.0005(6) 0.0003(6) -0.0006(6) O3C 0.0621(8) 0.0357(7) 0.0413(7) -0.0063(6) 0.0091(6) -0.0029(6) O4C 0.0484(8) 0.0403(8) 0.0564(8) -0.0143(6) -0.0074(6) -0.0048(6) O5C 0.0445(7) 0.0279(7) 0.0855(11) 0.0009(7) 0.0100(7) -0.0035(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1A O3A 1.4421(18) . ? C1A C5A 1.506(3) . ? C1A C2A 1.544(2) . ? C1A H1A 0.9800 . ? C2A N1A 1.487(2) . ? C2A C9A 1.506(3) . ? C2A H2A 0.9800 . ? C3A N1A 1.466(2) . ? C3A C4A 1.507(3) . ? C3A H3A1 0.9700 . ? C3A H3A2 0.9700 . ? C4A O1A 1.419(2) . ? C4A C5A 1.517(2) . ? C4A H4A 0.9800 . ? C5A O2A 1.424(2) . ? C5A H5A 0.9800 . ? C6A O2A 1.415(2) . ? C6A O3A 1.448(2) . ? C6A C7A 1.499(3) . ? C6A C8A 1.514(3) . ? C7A H7A1 0.9600 . ? C7A H7A2 0.9600 . ? C7A H7A3 0.9600 . ? C8A H8A1 0.9600 . ? C8A H8A2 0.9600 . ? C8A H8A3 0.9600 . ? C9A C10A 1.381(2) . ? C9A C14A 1.409(2) . ? C10A C11A 1.389(3) . ? C10A H10A 0.9300 . ? C11A C12A 1.385(3) . ? C11A H11A 0.9300 . ? C12A O4A 1.371(2) . ? C12A C13A 1.376(3) . ? C13A C14A 1.375(3) . ? C13A H13A 0.9300 . ? C14A O5A 1.358(2) . ? C15A C16D 1.4786 . ? C15A N1A 1.4858(17) . ? C15A C16A 1.5801 . ? C15A H15A 0.9700 . ? C15A H15B 0.9700 . ? C16A C17A 1.3900 . ? C16A C21A 1.3900 . ? C17A C18A 1.3900 . ? C17A H17A 0.9300 . ? C18A C19A 1.3900 . ? C18A H18A 0.9300 . ? C19A C20A 1.3900 . ? C19A H19A 0.9300 . ? C20A C21A 1.3900 . ? C20A H20A 0.9300 . ? C21A H21A 0.9300 . ? C16D C17D 1.3900 . ? C16D C21D 1.3900 . ? C17D C18D 1.3900 . ? C17D H17D 0.9300 . ? C18D C19D 1.3900 . ? C18D H18D 0.9300 . ? C19D C20D 1.3900 . ? C19D H19D 0.9300 . ? C20D C21D 1.3900 . ? C20D H20D 0.9300 . ? C21D H21D 0.9300 . ? C1B O3B 1.436(2) . ? C1B C5B 1.522(2) . ? C1B C2B 1.543(3) . ? C1B H1B 0.9800 . ? C2B N1B 1.491(2) . ? C2B C9B 1.508(2) . ? C2B H2B 0.9800 . ? C3B N1B 1.468(2) . ? C3B C4B 1.495(3) . ? C3B H3B1 0.9700 . ? C3B H3B2 0.9700 . ? C4B O1B 1.432(2) . ? C4B C5B 1.510(2) . ? C4B H4B 0.9800 . ? C5B O2B 1.423(2) . ? C5B H5B 0.9800 . ? C6B O2B 1.425(2) . ? C6B O3B 1.449(2) . ? C6B C7B 1.496(4) . ? C6B C8B 1.506(3) . ? C7B H7B1 0.9600 . ? C7B H7B2 0.9600 . ? C7B H7B3 0.9600 . ? C8B H8B1 0.9600 . ? C8B H8B2 0.9600 . ? C8B H8B3 0.9600 . ? C9B C10B 1.388(2) . ? C9B C14B 1.408(3) . ? C10B C11B 1.398(3) . ? C10B H10B 0.9300 . ? C11B C12B 1.385(3) . ? C11B H11B 0.9300 . ? C12B O4B 1.371(2) . ? C12B C13B 1.371(3) . ? C13B C14B 1.382(3) . ? C13B H13B 0.9300 . ? C14B O5B 1.362(2) . ? C15B N1B 1.481(2) . ? C15B C16B 1.499(3) . ? C15B H15C 0.9700 . ? C15B H15D 0.9700 . ? C16B C17B 1.373(3) . ? C16B C21B 1.374(3) . ? C17B C18B 1.394(3) . ? C17B H17B 0.9300 . ? C18B C19B 1.365(4) . ? C18B H18B 0.9300 . ? C19B C20B 1.337(5) . ? C19B H19B 0.9300 . ? C20B C21B 1.381(4) . ? C20B H20B 0.9300 . ? C21B H21B 0.9300 . ? C1C O3C 1.434(2) . ? C1C C5C 1.526(2) . ? C1C C2C 1.546(2) . ? C1C H1C 0.9800 . ? C2C N1C 1.485(2) . ? C2C C9C 1.526(2) . ? C2C H2C 0.9800 . ? C3C N1C 1.468(2) . ? C3C C4C 1.505(2) . ? C3C H3C1 0.9700 . ? C3C H3C2 0.9700 . ? C4C O1C 1.432(2) . ? C4C C5C 1.513(2) . ? C4C H4C 0.9800 . ? C5C O2C 1.421(2) . ? C5C H5C 0.9800 . ? C6C O2C 1.418(2) . ? C6C O3C 1.446(2) . ? C6C C7C 1.507(3) . ? C6C C8C 1.511(3) . ? C7C H7C1 0.9600 . ? C7C H7C2 0.9600 . ? C7C H7C3 0.9600 . ? C8C H8C1 0.9600 . ? C8C H8C2 0.9600 . ? C8C H8C3 0.9600 . ? C9C C10C 1.383(3) . ? C9C C14C 1.399(2) . ? C10C C11C 1.395(2) . ? C10C H10C 0.9300 . ? C11C C12C 1.382(3) . ? C11C H11C 0.9300 . ? C12C C13C 1.378(3) . ? C12C O5C 1.390(2) . ? C13C C14C 1.385(2) . ? C13C H13C 0.9300 . ? C14C O4C 1.360(2) . ? C15C N1C 1.487(2) . ? C15C C16C 1.505(3) . ? C15C H15E 0.9700 . ? C15C H15F 0.9700 . ? C16C C17C 1.374(3) . ? C16C C21C 1.381(3) . ? C17C C18C 1.396(4) . ? C17C H17C 0.9300 . ? C18C C19C 1.366(4) . ? C18C H18C 0.9300 . ? C19C C20C 1.349(4) . ? C19C H19C 0.9300 . ? C20C C21C 1.379(3) . ? C20C H20C 0.9300 . ? C21C H21C 0.9300 . ? O1A H1X 0.77(3) . ? O4A H9X 0.98(4) . ? O5A H2X 0.93(3) . ? O1B H4X 0.814(10) . ? O4B H7X 0.842(10) . ? O5B H8X 0.90(2) . ? O1C H6X 0.83(3) . ? O4C H5X 0.82(3) . ? O5C H3X 0.83(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3A C1A C5A 102.59(13) . . ? O3A C1A C2A 108.47(13) . . ? C5A C1A C2A 116.50(15) . . ? O3A C1A H1A 109.6 . . ? C5A C1A H1A 109.6 . . ? C2A C1A H1A 109.6 . . ? N1A C2A C9A 110.03(13) . . ? N1A C2A C1A 111.22(13) . . ? C9A C2A C1A 107.86(14) . . ? N1A C2A H2A 109.2 . . ? C9A C2A H2A 109.2 . . ? C1A C2A H2A 109.2 . . ? N1A C3A C4A 112.11(16) . . ? N1A C3A H3A1 109.2 . . ? C4A C3A H3A1 109.2 . . ? N1A C3A H3A2 109.2 . . ? C4A C3A H3A2 109.2 . . ? H3A1 C3A H3A2 107.9 . . ? O1A C4A C3A 112.54(16) . . ? O1A C4A C5A 104.67(16) . . ? C3A C4A C5A 112.19(15) . . ? O1A C4A H4A 109.1 . . ? C3A C4A H4A 109.1 . . ? C5A C4A H4A 109.1 . . ? O2A C5A C1A 102.36(13) . . ? O2A C5A C4A 110.42(15) . . ? C1A C5A C4A 114.70(15) . . ? O2A C5A H5A 109.7 . . ? C1A C5A H5A 109.7 . . ? C4A C5A H5A 109.7 . . ? O2A C6A O3A 105.47(12) . . ? O2A C6A C7A 108.44(18) . . ? O3A C6A C7A 109.89(17) . . ? O2A C6A C8A 112.01(17) . . ? O3A C6A C8A 107.70(18) . . ? C7A C6A C8A 113.06(18) . . ? C6A C7A H7A1 109.5 . . ? C6A C7A H7A2 109.5 . . ? H7A1 C7A H7A2 109.5 . . ? C6A C7A H7A3 109.5 . . ? H7A1 C7A H7A3 109.5 . . ? H7A2 C7A H7A3 109.5 . . ? C6A C8A H8A1 109.5 . . ? C6A C8A H8A2 109.5 . . ? H8A1 C8A H8A2 109.5 . . ? C6A C8A H8A3 109.5 . . ? H8A1 C8A H8A3 109.5 . . ? H8A2 C8A H8A3 109.5 . . ? C10A C9A C14A 117.98(17) . . ? C10A C9A C2A 122.48(15) . . ? C14A C9A C2A 119.37(15) . . ? C9A C10A C11A 121.73(17) . . ? C9A C10A H10A 119.1 . . ? C11A C10A H10A 119.1 . . ? C12A C11A C10A 119.12(17) . . ? C12A C11A H11A 120.4 . . ? C10A C11A H11A 120.4 . . ? O4A C12A C13A 121.77(18) . . ? O4A C12A C11A 118.10(18) . . ? C13A C12A C11A 120.12(18) . . ? C14A C13A C12A 120.73(17) . . ? C14A C13A H13A 119.6 . . ? C12A C13A H13A 119.6 . . ? O5A C14A C13A 118.11(16) . . ? O5A C14A C9A 121.57(17) . . ? C13A C14A C9A 120.32(17) . . ? C16D C15A N1A 117.11(6) . . ? C16D C15A C16A 10.6 . . ? N1A C15A C16A 109.66(6) . . ? C16D C15A H15A 111.8 . . ? N1A C15A H15A 109.7 . . ? C16A C15A H15A 109.7 . . ? C16D C15A H15B 99.5 . . ? N1A C15A H15B 109.7 . . ? C16A C15A H15B 109.7 . . ? H15A C15A H15B 108.2 . . ? C17A C16A C21A 120.0 . . ? C17A C16A C15A 120.8 . . ? C21A C16A C15A 118.7 . . ? C18A C17A C16A 120.0 . . ? C18A C17A H17A 120.0 . . ? C16A C17A H17A 120.0 . . ? C17A C18A C19A 120.0 . . ? C17A C18A H18A 120.0 . . ? C19A C18A H18A 120.0 . . ? C20A C19A C18A 120.0 . . ? C20A C19A H19A 120.0 . . ? C18A C19A H19A 120.0 . . ? C19A C20A C21A 120.0 . . ? C19A C20A H20A 120.0 . . ? C21A C20A H20A 120.0 . . ? C20A C21A C16A 120.0 . . ? C20A C21A H21A 120.0 . . ? C16A C21A H21A 120.0 . . ? C17D C16D C21D 120.0 . . ? C17D C16D C15A 118.7 . . ? C21D C16D C15A 121.2 . . ? C18D C17D C16D 120.0 . . ? C18D C17D H17D 120.0 . . ? C16D C17D H17D 120.0 . . ? C17D C18D C19D 120.0 . . ? C17D C18D H18D 120.0 . . ? C19D C18D H18D 120.0 . . ? C18D C19D C20D 120.0 . . ? C18D C19D H19D 120.0 . . ? C20D C19D H19D 120.0 . . ? C21D C20D C19D 120.0 . . ? C21D C20D H20D 120.0 . . ? C19D C20D H20D 120.0 . . ? C20D C21D C16D 120.0 . . ? C20D C21D H21D 120.0 . . ? C16D C21D H21D 120.0 . . ? O3B C1B C5B 102.32(13) . . ? O3B C1B C2B 108.34(13) . . ? C5B C1B C2B 115.83(14) . . ? O3B C1B H1B 110.0 . . ? C5B C1B H1B 110.0 . . ? C2B C1B H1B 110.0 . . ? N1B C2B C9B 109.87(14) . . ? N1B C2B C1B 110.36(12) . . ? C9B C2B C1B 108.34(13) . . ? N1B C2B H2B 109.4 . . ? C9B C2B H2B 109.4 . . ? C1B C2B H2B 109.4 . . ? N1B C3B C4B 112.39(13) . . ? N1B C3B H3B1 109.1 . . ? C4B C3B H3B1 109.1 . . ? N1B C3B H3B2 109.1 . . ? C4B C3B H3B2 109.1 . . ? H3B1 C3B H3B2 107.9 . . ? O1B C4B C3B 112.01(15) . . ? O1B C4B C5B 105.41(14) . . ? C3B C4B C5B 112.90(14) . . ? O1B C4B H4B 108.8 . . ? C3B C4B H4B 108.8 . . ? C5B C4B H4B 108.8 . . ? O2B C5B C4B 110.20(14) . . ? O2B C5B C1B 102.54(13) . . ? C4B C5B C1B 115.05(15) . . ? O2B C5B H5B 109.6 . . ? C4B C5B H5B 109.6 . . ? C1B C5B H5B 109.6 . . ? O2B C6B O3B 104.76(14) . . ? O2B C6B C7B 111.77(18) . . ? O3B C6B C7B 108.29(18) . . ? O2B C6B C8B 108.80(18) . . ? O3B C6B C8B 109.05(18) . . ? C7B C6B C8B 113.8(2) . . ? C6B C7B H7B1 109.5 . . ? C6B C7B H7B2 109.5 . . ? H7B1 C7B H7B2 109.5 . . ? C6B C7B H7B3 109.5 . . ? H7B1 C7B H7B3 109.5 . . ? H7B2 C7B H7B3 109.5 . . ? C6B C8B H8B1 109.5 . . ? C6B C8B H8B2 109.5 . . ? H8B1 C8B H8B2 109.5 . . ? C6B C8B H8B3 109.5 . . ? H8B1 C8B H8B3 109.5 . . ? H8B2 C8B H8B3 109.5 . . ? C10B C9B C14B 117.56(16) . . ? C10B C9B C2B 123.23(16) . . ? C14B C9B C2B 119.15(15) . . ? C9B C10B C11B 121.52(19) . . ? C9B C10B H10B 119.2 . . ? C11B C10B H10B 119.2 . . ? C12B C11B C10B 119.22(18) . . ? C12B C11B H11B 120.4 . . ? C10B C11B H11B 120.4 . . ? O4B C12B C13B 117.6(2) . . ? O4B C12B C11B 122.1(2) . . ? C13B C12B C11B 120.33(17) . . ? C12B C13B C14B 120.5(2) . . ? C12B C13B H13B 119.8 . . ? C14B C13B H13B 119.8 . . ? O5B C14B C13B 117.50(17) . . ? O5B C14B C9B 121.68(15) . . ? C13B C14B C9B 120.81(17) . . ? N1B C15B C16B 114.59(14) . . ? N1B C15B H15C 108.6 . . ? C16B C15B H15C 108.6 . . ? N1B C15B H15D 108.6 . . ? C16B C15B H15D 108.6 . . ? H15C C15B H15D 107.6 . . ? C17B C16B C21B 117.75(19) . . ? C17B C16B C15B 120.83(17) . . ? C21B C16B C15B 121.36(19) . . ? C16B C17B C18B 120.8(2) . . ? C16B C17B H17B 119.6 . . ? C18B C17B H17B 119.6 . . ? C19B C18B C17B 119.5(2) . . ? C19B C18B H18B 120.3 . . ? C17B C18B H18B 120.3 . . ? C20B C19B C18B 120.4(2) . . ? C20B C19B H19B 119.8 . . ? C18B C19B H19B 119.8 . . ? C19B C20B C21B 120.4(3) . . ? C19B C20B H20B 119.8 . . ? C21B C20B H20B 119.8 . . ? C16B C21B C20B 121.2(3) . . ? C16B C21B H21B 119.4 . . ? C20B C21B H21B 119.4 . . ? O3C C1C C5C 102.39(13) . . ? O3C C1C C2C 109.15(14) . . ? C5C C1C C2C 116.06(13) . . ? O3C C1C H1C 109.6 . . ? C5C C1C H1C 109.6 . . ? C2C C1C H1C 109.6 . . ? N1C C2C C9C 110.37(13) . . ? N1C C2C C1C 110.12(13) . . ? C9C C2C C1C 108.04(13) . . ? N1C C2C H2C 109.4 . . ? C9C C2C H2C 109.4 . . ? C1C C2C H2C 109.4 . . ? N1C C3C C4C 112.24(13) . . ? N1C C3C H3C1 109.2 . . ? C4C C3C H3C1 109.2 . . ? N1C C3C H3C2 109.2 . . ? C4C C3C H3C2 109.2 . . ? H3C1 C3C H3C2 107.9 . . ? O1C C4C C3C 112.85(15) . . ? O1C C4C C5C 106.21(14) . . ? C3C C4C C5C 112.32(14) . . ? O1C C4C H4C 108.4 . . ? C3C C4C H4C 108.4 . . ? C5C C4C H4C 108.4 . . ? O2C C5C C4C 108.77(14) . . ? O2C C5C C1C 102.75(14) . . ? C4C C5C C1C 116.50(14) . . ? O2C C5C H5C 109.5 . . ? C4C C5C H5C 109.5 . . ? C1C C5C H5C 109.5 . . ? O2C C6C O3C 104.88(14) . . ? O2C C6C C7C 108.69(19) . . ? O3C C6C C7C 109.60(19) . . ? O2C C6C C8C 111.86(18) . . ? O3C C6C C8C 108.39(18) . . ? C7C C6C C8C 113.1(2) . . ? C6C C7C H7C1 109.5 . . ? C6C C7C H7C2 109.5 . . ? H7C1 C7C H7C2 109.5 . . ? C6C C7C H7C3 109.5 . . ? H7C1 C7C H7C3 109.5 . . ? H7C2 C7C H7C3 109.5 . . ? C6C C8C H8C1 109.5 . . ? C6C C8C H8C2 109.5 . . ? H8C1 C8C H8C2 109.5 . . ? C6C C8C H8C3 109.5 . . ? H8C1 C8C H8C3 109.5 . . ? H8C2 C8C H8C3 109.5 . . ? C10C C9C C14C 118.30(15) . . ? C10C C9C C2C 122.54(15) . . ? C14C C9C C2C 119.06(15) . . ? C9C C10C C11C 121.46(17) . . ? C9C C10C H10C 119.3 . . ? C11C C10C H10C 119.3 . . ? C12C C11C C10C 118.86(17) . . ? C12C C11C H11C 120.6 . . ? C10C C11C H11C 120.6 . . ? C13C C12C C11C 120.81(15) . . ? C13C C12C O5C 117.87(17) . . ? C11C C12C O5C 121.25(16) . . ? C12C C13C C14C 119.86(17) . . ? C12C C13C H13C 120.1 . . ? C14C C13C H13C 120.1 . . ? O4C C14C C13C 117.22(16) . . ? O4C C14C C9C 122.16(15) . . ? C13C C14C C9C 120.62(16) . . ? N1C C15C C16C 111.98(15) . . ? N1C C15C H15E 109.2 . . ? C16C C15C H15E 109.2 . . ? N1C C15C H15F 109.2 . . ? C16C C15C H15F 109.2 . . ? H15E C15C H15F 107.9 . . ? C17C C16C C21C 117.5(2) . . ? C17C C16C C15C 121.45(18) . . ? C21C C16C C15C 121.03(19) . . ? C16C C17C C18C 120.5(2) . . ? C16C C17C H17C 119.7 . . ? C18C C17C H17C 119.7 . . ? C19C C18C C17C 120.3(2) . . ? C19C C18C H18C 119.9 . . ? C17C C18C H18C 119.9 . . ? C20C C19C C18C 119.7(3) . . ? C20C C19C H19C 120.1 . . ? C18C C19C H19C 120.1 . . ? C19C C20C C21C 120.3(2) . . ? C19C C20C H20C 119.9 . . ? C21C C20C H20C 119.9 . . ? C20C C21C C16C 121.6(2) . . ? C20C C21C H21C 119.2 . . ? C16C C21C H21C 119.2 . . ? C3A N1A C15A 110.49(13) . . ? C3A N1A C2A 110.86(13) . . ? C15A N1A C2A 110.02(12) . . ? C3B N1B C15B 109.77(13) . . ? C3B N1B C2B 109.72(13) . . ? C15B N1B C2B 109.04(12) . . ? C3C N1C C2C 109.99(13) . . ? C3C N1C C15C 109.63(13) . . ? C2C N1C C15C 111.15(13) . . ? C4A O1A H1X 110.4(19) . . ? C6A O2A C5A 106.22(13) . . ? C1A O3A C6A 108.34(13) . . ? C12A O4A H9X 120(2) . . ? C14A O5A H2X 105.6(16) . . ? C4B O1B H4X 109.5(19) . . ? C5B O2B C6B 106.45(13) . . ? C1B O3B C6B 109.54(12) . . ? C12B O4B H7X 112(2) . . ? C14B O5B H8X 106.6(14) . . ? C4C O1C H6X 111.9(16) . . ? C6C O2C C5C 106.27(13) . . ? C1C O3C C6C 109.56(13) . . ? C14C O4C H5X 105.5(17) . . ? C12C O5C H3X 107.1(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3A C1A C2A N1A 157.37(13) . . . . ? C5A C1A C2A N1A 42.33(19) . . . . ? O3A C1A C2A C9A -81.89(16) . . . . ? C5A C1A C2A C9A 163.07(14) . . . . ? N1A C3A C4A O1A 62.7(2) . . . . ? N1A C3A C4A C5A -55.0(2) . . . . ? O3A C1A C5A O2A -34.20(16) . . . . ? C2A C1A C5A O2A 84.10(16) . . . . ? O3A C1A C5A C4A -153.80(15) . . . . ? C2A C1A C5A C4A -35.5(2) . . . . ? O1A C4A C5A O2A 163.29(15) . . . . ? C3A C4A C5A O2A -74.4(2) . . . . ? O1A C4A C5A C1A -81.71(19) . . . . ? C3A C4A C5A C1A 40.6(2) . . . . ? N1A C2A C9A C10A -138.81(16) . . . . ? C1A C2A C9A C10A 99.72(17) . . . . ? N1A C2A C9A C14A 46.09(19) . . . . ? C1A C2A C9A C14A -75.38(17) . . . . ? C14A C9A C10A C11A 0.3(2) . . . . ? C2A C9A C10A C11A -174.88(15) . . . . ? C9A C10A C11A C12A -0.8(3) . . . . ? C10A C11A C12A O4A -178.47(16) . . . . ? C10A C11A C12A C13A 0.7(3) . . . . ? O4A C12A C13A C14A 178.98(16) . . . . ? C11A C12A C13A C14A -0.1(3) . . . . ? C12A C13A C14A O5A 179.37(16) . . . . ? C12A C13A C14A C9A -0.3(3) . . . . ? C10A C9A C14A O5A -179.44(16) . . . . ? C2A C9A C14A O5A -4.1(2) . . . . ? C10A C9A C14A C13A 0.3(2) . . . . ? C2A C9A C14A C13A 175.59(15) . . . . ? C16D C15A C16A C17A -60.7 . . . . ? N1A C15A C16A C17A 75.55(8) . . . . ? C16D C15A C16A C21A 111.1 . . . . ? N1A C15A C16A C21A -112.71(8) . . . . ? C21A C16A C17A C18A 0.0 . . . . ? C15A C16A C17A C18A 171.6 . . . . ? C16A C17A C18A C19A 0.0 . . . . ? C17A C18A C19A C20A 0.0 . . . . ? C18A C19A C20A C21A 0.0 . . . . ? C19A C20A C21A C16A 0.0 . . . . ? C17A C16A C21A C20A 0.0 . . . . ? C15A C16A C21A C20A -171.8 . . . . ? N1A C15A C16D C17D 82.23(8) . . . . ? C16A C15A C16D C17D 129.3 . . . . ? N1A C15A C16D C21D -94.41(9) . . . . ? C16A C15A C16D C21D -47.4 . . . . ? C21D C16D C17D C18D 0.0 . . . . ? C15A C16D C17D C18D -176.7 . . . . ? C16D C17D C18D C19D 0.0 . . . . ? C17D C18D C19D C20D 0.0 . . . . ? C18D C19D C20D C21D 0.0 . . . . ? C19D C20D C21D C16D 0.0 . . . . ? C17D C16D C21D C20D 0.0 . . . . ? C15A C16D C21D C20D 176.6 . . . . ? O3B C1B C2B N1B 158.60(12) . . . . ? C5B C1B C2B N1B 44.38(19) . . . . ? O3B C1B C2B C9B -81.07(16) . . . . ? C5B C1B C2B C9B 164.71(14) . . . . ? N1B C3B C4B O1B 65.11(17) . . . . ? N1B C3B C4B C5B -53.69(19) . . . . ? O1B C4B C5B O2B 159.98(14) . . . . ? C3B C4B C5B O2B -77.45(18) . . . . ? O1B C4B C5B C1B -84.72(18) . . . . ? C3B C4B C5B C1B 37.9(2) . . . . ? O3B C1B C5B O2B -32.42(17) . . . . ? C2B C1B C5B O2B 85.19(17) . . . . ? O3B C1B C5B C4B -152.06(15) . . . . ? C2B C1B C5B C4B -34.4(2) . . . . ? N1B C2B C9B C10B -134.16(18) . . . . ? C1B C2B C9B C10B 105.21(19) . . . . ? N1B C2B C9B C14B 48.7(2) . . . . ? C1B C2B C9B C14B -71.96(19) . . . . ? C14B C9B C10B C11B 1.5(3) . . . . ? C2B C9B C10B C11B -175.76(17) . . . . ? C9B C10B C11B C12B 0.8(3) . . . . ? C10B C11B C12B O4B 177.40(19) . . . . ? C10B C11B C12B C13B -1.6(3) . . . . ? O4B C12B C13B C14B -178.87(18) . . . . ? C11B C12B C13B C14B 0.2(3) . . . . ? C12B C13B C14B O5B -176.99(19) . . . . ? C12B C13B C14B C9B 2.1(3) . . . . ? C10B C9B C14B O5B 176.17(18) . . . . ? C2B C9B C14B O5B -6.5(3) . . . . ? C10B C9B C14B C13B -2.9(3) . . . . ? C2B C9B C14B C13B 174.44(17) . . . . ? N1B C15B C16B C17B -119.96(19) . . . . ? N1B C15B C16B C21B 62.9(3) . . . . ? C21B C16B C17B C18B 1.0(3) . . . . ? C15B C16B C17B C18B -176.27(18) . . . . ? C16B C17B C18B C19B -0.2(3) . . . . ? C17B C18B C19B C20B -1.0(4) . . . . ? C18B C19B C20B C21B 1.4(5) . . . . ? C17B C16B C21B C20B -0.7(4) . . . . ? C15B C16B C21B C20B 176.6(2) . . . . ? C19B C20B C21B C16B -0.5(5) . . . . ? O3C C1C C2C N1C 157.24(12) . . . . ? C5C C1C C2C N1C 42.2(2) . . . . ? O3C C1C C2C C9C -82.15(16) . . . . ? C5C C1C C2C C9C 162.85(15) . . . . ? N1C C3C C4C O1C 67.65(19) . . . . ? N1C C3C C4C C5C -52.4(2) . . . . ? O1C C4C C5C O2C 155.14(13) . . . . ? C3C C4C C5C O2C -81.04(17) . . . . ? O1C C4C C5C C1C -89.40(18) . . . . ? C3C C4C C5C C1C 34.4(2) . . . . ? O3C C1C C5C O2C -30.67(15) . . . . ? C2C C1C C5C O2C 88.10(17) . . . . ? O3C C1C C5C C4C -149.45(15) . . . . ? C2C C1C C5C C4C -30.7(2) . . . . ? N1C C2C C9C C10C -135.63(16) . . . . ? C1C C2C C9C C10C 103.91(17) . . . . ? N1C C2C C9C C14C 48.06(19) . . . . ? C1C C2C C9C C14C -72.39(19) . . . . ? C14C C9C C10C C11C 1.9(2) . . . . ? C2C C9C C10C C11C -174.46(15) . . . . ? C9C C10C C11C C12C 0.5(2) . . . . ? C10C C11C C12C C13C -1.5(2) . . . . ? C10C C11C C12C O5C 175.35(15) . . . . ? C11C C12C C13C C14C 0.1(2) . . . . ? O5C C12C C13C C14C -176.89(15) . . . . ? C12C C13C C14C O4C -177.60(15) . . . . ? C12C C13C C14C C9C 2.4(2) . . . . ? C10C C9C C14C O4C 176.68(15) . . . . ? C2C C9C C14C O4C -6.9(2) . . . . ? C10C C9C C14C C13C -3.3(2) . . . . ? C2C C9C C14C C13C 173.13(15) . . . . ? N1C C15C C16C C17C 69.1(2) . . . . ? N1C C15C C16C C21C -111.66(19) . . . . ? C21C C16C C17C C18C 0.5(3) . . . . ? C15C C16C C17C C18C 179.8(2) . . . . ? C16C C17C C18C C19C 0.1(4) . . . . ? C17C C18C C19C C20C -1.0(4) . . . . ? C18C C19C C20C C21C 1.3(4) . . . . ? C19C C20C C21C C16C -0.7(3) . . . . ? C17C C16C C21C C20C -0.2(3) . . . . ? C15C C16C C21C C20C -179.44(18) . . . . ? C4A C3A N1A C15A -174.37(12) . . . . ? C4A C3A N1A C2A 63.39(18) . . . . ? C16D C15A N1A C3A 87.31(12) . . . . ? C16A C15A N1A C3A 79.10(11) . . . . ? C16D C15A N1A C2A -149.96(9) . . . . ? C16A C15A N1A C2A -158.17(9) . . . . ? C9A C2A N1A C3A -174.77(14) . . . . ? C1A C2A N1A C3A -55.32(18) . . . . ? C9A C2A N1A C15A 62.71(16) . . . . ? C1A C2A N1A C15A -177.83(13) . . . . ? C4B C3B N1B C15B -175.18(14) . . . . ? C4B C3B N1B C2B 65.01(17) . . . . ? C16B C15B N1B C3B 72.86(19) . . . . ? C16B C15B N1B C2B -166.92(15) . . . . ? C9B C2B N1B C3B -177.98(14) . . . . ? C1B C2B N1B C3B -58.58(16) . . . . ? C9B C2B N1B C15B 61.77(17) . . . . ? C1B C2B N1B C15B -178.83(14) . . . . ? C4C C3C N1C C2C 66.63(18) . . . . ? C4C C3C N1C C15C -170.86(15) . . . . ? C9C C2C N1C C3C -178.65(13) . . . . ? C1C C2C N1C C3C -59.45(17) . . . . ? C9C C2C N1C C15C 59.74(17) . . . . ? C1C C2C N1C C15C 178.94(14) . . . . ? C16C C15C N1C C3C 70.64(19) . . . . ? C16C C15C N1C C2C -167.54(14) . . . . ? O3A C6A O2A C5A -28.36(18) . . . . ? C7A C6A O2A C5A -146.03(17) . . . . ? C8A C6A O2A C5A 88.52(19) . . . . ? C1A C5A O2A C6A 39.06(17) . . . . ? C4A C5A O2A C6A 161.61(15) . . . . ? C5A C1A O3A C6A 17.69(18) . . . . ? C2A C1A O3A C6A -106.13(16) . . . . ? O2A C6A O3A C1A 5.54(18) . . . . ? C7A C6A O3A C1A 122.23(18) . . . . ? C8A C6A O3A C1A -114.22(17) . . . . ? C4B C5B O2B C6B 161.49(15) . . . . ? C1B C5B O2B C6B 38.53(19) . . . . ? O3B C6B O2B C5B -29.2(2) . . . . ? C7B C6B O2B C5B 87.8(2) . . . . ? C8B C6B O2B C5B -145.72(19) . . . . ? C5B C1B O3B C6B 15.39(19) . . . . ? C2B C1B O3B C6B -107.45(16) . . . . ? O2B C6B O3B C1B 7.4(2) . . . . ? C7B C6B O3B C1B -112.02(19) . . . . ? C8B C6B O3B C1B 123.72(19) . . . . ? O3C C6C O2C C5C -30.86(18) . . . . ? C7C C6C O2C C5C -148.01(18) . . . . ? C8C C6C O2C C5C 86.4(2) . . . . ? C4C C5C O2C C6C 162.48(14) . . . . ? C1C C5C O2C C6C 38.42(16) . . . . ? C5C C1C O3C C6C 12.59(17) . . . . ? C2C C1C O3C C6C -110.94(15) . . . . ? O2C C6C O3C C1C 10.19(19) . . . . ? C7C C6C O3C C1C 126.71(19) . . . . ? C8C C6C O3C C1C -109.44(18) . . . . ? _diffrn_measured_fraction_theta_max 0.611 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 0.189 _refine_diff_density_min -0.144 _refine_diff_density_rms 0.029 _database_code_depnum_ccdc_archive 'CCDC 931865'